Embarrassing Punishment – A Transgender Romance Story

  • Title: Embarrassing Punishment
  • Subtitle: A Transgender Romance Story
  • Author: Yu Sakurazawa
  • Category: transgender, mtf

Jacob King is the protagonist of the story. He is 26 years old, has brown hair and aquamarine blue eyes. Jacob is 5’6 and is thin as a rake. He is boastful and claims that if made president of the Blue Bonnets Association, he’ll be able to extract maintenance dues from a habitual defaulter in 3 months. Jacob also says that if he fails in his self-imposed challenge, he will live the rest of his life as a woman and even take female hormones. Jacob fails in the bet, which forces him to transition into a woman. Transitioning affects his life negatively: he loses job and his wife leaves him. Life changes for the better when Jake meets the owner of an adult movie house. Jacob moves to LA and starts appearing in adult films.

Embarrassing Punishment

Chapter 1 – Clash of Egos

I was having drinks with a few other residents of Blue Bonnets, our apartment block. My booze pals for the night were sixty three year old Thomas Owens, a retired bank manager and Mason Scott, a thirtyish ginger who worked as a restaurant manager. Since Blue Bonnets was one of the few apartment complexes in our little town in Texas, we had formulated a Management Committee (MC) with its own rules and regulations. Mr. Owens was the President of the association and Scott doubled as secretary cum treasurer.

Since my wife Natalie wasn’t present at our little party, I had already had a pint too many. I was thought of as “condescending” and “overconfident”; I felt invincibly so now. “You guys from the MC are useless!” I said taking a swig from the whiskey bottle “you haven’t been able to collect dues from the habitual defaulter in 3 long years! I would have done it in 3 months flat!”

The habitual defaulter I was talking about was Ahmed Khan, an Indian immigrant. Ahmed’s maintenance dues over the last three years had soared to hundreds of dollars.

“We’ve tried our best, King” replied Mr. Owens quietly “but it hasn’t been possible”.

“Why not?” I demanded “you should have cut off his water and electricity supply! Had you deprived Ahmed of the rights and facilities enjoyed by the other residents, he would have coughed up the money immediately!”

“We couldn’t do that” said Mr. Owens “Ahmed Khan’s case is a bit different”.

“Rubbish!” I said “you’re giving excuses! The MC is useless, that is the Gospel truth. Had I been the president, I would have extracted the dues from the guy in three months!”

“Fine” said Mr. Owens growing red with rage “you become the president. I pass on the baton to you. I shall be handing Mason my resignation letter tonight”.

“Good decision, Mr. Owens” I said cockily “you will be amazed at how quickly I accomplish the mission!”

“What if you fail?” asked Mr. Owens with passive belligerence.

“I shall not fail” I said with zest “If I do, I will live the rest of my life as a goddamn woman and even take female hormones!”


Scott chuckled embarrassingly at my ridiculous declaration. But Mr. Owens didn’t bat an eyelid.

“Say you’ll become a woman in writing and also put your signature” he said. He opened his briefcase and gave me a sheet of paper and a pen.

With a slightly quivering hand, I wrote the follows.

“This contract entered into on the 13th day of December 2017 by William Owens, retired employee at Dollars Bank, 45, Blue Bonnets Apartment, Texas and Jacob King, teacher at Texas High, 45 Blue Bonnets Apartment, Texas, do hereby agree to the terms given and described below:

1) I, Jacob King, promise to extract dues from defaulter Ahmed Khan by the 13th of March 2018, failing to do which I shall dress and live as a woman for the rest of my life.

2) I, Jacob King, also agree to take female hormones to become entirely feminized in case I fail in my mission of extracting dues from defaulter Ahmed Khan before the 13th of March 2018.

I showed the lines I had penned to Mr. Owens and Scott. Mr. Owens nodded in approval. Scott showed no reaction. But as I picked up the pen again to sign, Scott rushed to my side and grabbed my hand.

“You’re making a mistake, King” he said “Ahmed Khan isn’t the typical defaulter…for many reasons. It might be nearly impossible to extract dues from him…”

I smiled benignly at Scott. He, a soft-spoken hulk of a man, was one of the kindest persons on earth. The residents of Blue Bonnets called him “Gentle Giant” for a good reason.

“Nothing is impossible, my friend” I said “especially for Jacob King”.

“Maybe” said Scott “but please don’t sign”. His grip on my hand tightened.

My temper got the better of me. “Leave me alone, Scott!” I said releasing my hand from his grasp “I’m a 26 year old man, not a child! I take responsibility for my actions!”

Scott reluctantly let go of my arm and took his seat beside Mr. Owens. As I signed, a slow, sadistic smile spread across Mr. Owens’s face. “I hope the braggart bastard fails and pays” he seemed to be thinking. Scott just sat resignedly, holding his head in his hands.


The next morning, Scott came to my apartment to hand me the appointment letter. “You’re the president of the association now” he said, “but I wish you hadn’t created and signed that silly contract last night”.

“Why not?” I demanded “I’m going to win anyway”.

“I hope you do” said Scott sincerely “but it isn’t easy to collect dues from Ahmed Khan. He is a Muslim AND an immigrant”.

“What does that have to do with anything?” I said baffled “he should be treated like any other defaulter”.

“You are too naïve, King” Scott chided “it’s hard to treat Ahmed like any other defaulter. The president of the US has made too many remarks against immigrants and Muslims. If we cut off Ahmed’s water and electricity supplies, and deprive him of other rights and facilities that the other residents of Blue Bonnets enjoy, it will appear that we are discriminating against him”.

“The situation is a tricky one” I said, “but I can handle it”.


In the evening after school, I freshened up and went straight to Ahmed Khan’s house. His young and pretty wife opened the door. She was crying so copiously that mascara had rolled down her cheeks. Mrs. Khan’s hair was disheveled and framed her face like Medusa’s locks.

“What happened, Mrs. Khan?” I asked shocked by the young woman’s appearance.

“The bastard left me” was Fatima Khan’s response.

I surmised that she was referring to her husband. I waited for Fatima to say more.

“My parents warned me against marrying him” she continued “they didn’t trust Ahmed Khan one little bit. Also, they couldn’t understand why I would want to marry someone thirty years older…but Ahmed was so disarmingly charming and such a glib talker, that I fell in love with him and accepted his marriage proposal…my parents disowned me after my marriage…”

“I’m sorry to hear that, Mrs. Khan” I said somewhat impatiently “but what’s wrong at the moment? Where is Mr. Khan?”

“He has fled to Oman to be with his family” said Fatima breaking into tears again “I believe he already had a wife and grown children before he married me. And now I have been abandoned in their favor. My parents will not take me back. I am broke and don’t have a job. I’ll soon have to find one, or else I’ll starve!”

My stomach lurched as I digested this piece of information. With events having taken a turn for the worse, it would be harder to extract maintenance dues. Yet I boldly persevered.

“Mrs. Khan, your husband hasn’t paid the maintenance money for 3 years” I said “it has soared to hundreds of dollars. Are you aware of this?”

The shock on Fatima’s Khan’s face was evident. “What?!” she said “Oh no!”

“Yes, Mrs. Khan” I said “I request you to pay the amount ASAP”.

“But I’m broke, Mr. King!” Fatima cried “I don’t have a dime. That bastard even sold my gold earrings, which were my only possession!”

“I understand, Mrs. Khan” I said, my mouth going dry “but can’t you arrange for the money somehow…maybe contact your parents in India?”

“No way!” said Mrs. Khan “they don’t want to see my face ever again, do you think they’ll lend me money?!”

“I guess not” I said.

“I request the association to give me time” said Fatima composing herself “I’ll earn an honest living and clear the dues. But it may not happen overnight”.


Three months passed in the batting of an eyelid. Ahmed Khan didn’t return. Fatima Khan had found herself a job, but hadn’t made enough money to pay her maintenance dues. I couldn’t bring myself to force an abandoned woman to beg, borrow or steal and cough up the money. I was assertive, but not heartless.

On the night of 13th March 2018, Mr. Owens came to my apartment. “You’ve lost the bet, King” he said simply “you’ll now have to keep your side of the bargain”.

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