Embarrassing Punishment is a transgender romance novella written by Yu Sakurazawa.
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.
Jacob King/Jenny Bubbles: is the protagonist of the story. He is 26 years old and has brown hair and aquamarine blue eyes. Jacob is 5’6 and as 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 the 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 becomes Jenny Bubbles, a famous adult movie star.
Mason King: is a resident of Blue Bonnet’s association. He is tall, well-built ginger. Mason is soft-spoken and kind-hearted, which earns him the moniker “Gentle Giant”. Mason tries to dissuade Jacob from committing to the ridiculous bet when drunk but fails. When Jacob faces troubles after transitioning, Mason helps him out. He wants to be Jacob’s friend and hang out with him. Mason supports Jacob when the whole town discriminates against her.
Natalie King: is Jacob’s wife. Natalie is a slim, pale blonde who works as a nurse. She supports Jacob during the initial days of his feminization but soon leaves him for Caleb Summers, a doctor. Natalie loves Jacob but is unable to deal with his feminization. She also wishes to have a baby, owing to which she finds another man.
Ahmed Khan: is a resident of the Blue Bonnets Association. He is in his mid-50s, but is married to a much younger woman. Ahmed is a habitual defaulter who doesn’t pay his maintenance dues to the Apartment Association. Jacob takes up the challenge of extracting the dues from Ahmed within 3 months but finds out that Ahmed has fled to Oman, leaving his penniless wife behind. As a result of this, Jacob fails in his bet and is forced to transition into a woman.
Fatima Khan: is the young and pretty wife of Ahmed Khan. She marries Ahmed Khan against her parents’ wishes and moves with him to Texas. Fatima is devastated when Ahmed discloses that he already has a wife and children. She is subsequently abandoned by Ahmed and is forced to fend for herself. Fatima is broke and is unable to pay the maintenance dues.
Thomas Owens: is the former president of the Blue Bonnets Association. He is a careworn retired bank manager in his 60s. Owens has zero-tolerance for overconfident young people. He is egoistic and vindictive and doesn’t forgive easily. Owens is enraged when Jacob calls the Management Committee “useless” and brags about being able to do a better job if made the president. He talks Jacob into making a bet which leads to his feminization. Owens’s rage changes Jacob’s life forever.
Florence White: is Jacob’s colleague and headteacher. She is in her mid-50s and is a regular churchgoer. Mrs. White has zero tolerance towards those who show willful disobedience against God and castigates Jacob when he shows up to school dressed as a woman. Jacob’s views offend Mrs. White, who spreads malicious rumors about him. As a result, the entire faculty of the school turns against Jacob.
Colin Johnson: is the principal of the school Jacob works in. He disapproves of Jacob’s cross-dressing and his argument with a senior teacher (Mrs. White). Mr. Johnson passively protests by not responding to Jake’s greetings and smiles.
William Parker: is the dean of the school Jacob works in. He summons Jake to his cabin and warns him against cross-dressing. Mr. Parker believes that “bizarre behavior” by the faculty will negatively affect impressionable young students. Mr. Parker is concerned about the image of the school. When Jake continues cross-dressing, Mr. Parker fires her.
Taylor Wells: is the watchman of Blue Bonnets. He is a cocky, impish young man. When Jake is transitioning, Wells insults her as a result of which he is fired. Wells subsequently becomes an agent for an LA-based adult movie producer. In spite of having insulted Jacob, Wells finds her sexy and introduces her to the movie producer.
Caleb Summers: is a doctor in the hospital Natalie works in. Caleb was Natalie and Jake’s classmate in high school. Caleb was tall, athletic, smart and interested in Natalie. Yet he lost her to the less successful Jacob. Caleb succeeds in winning Natalie over after Jake’s feminization and marries her.
Liam Castro: is an adult movie producer based in Los Angles. He owns a production company called Sassy Love. He is in his mid-50s, is fat and has a scruffy beard. Liam meets Jake through Taylor Wells. He takes her to LA and casts her in his porn movies. Liam names Jake “Jenny Bubbles”. He succeeds in making Jenny a star.
Martha Matilda: is a porn star. She is a tall blonde with big surgically enhanced boobs. Martha acts with Jenny in her first movie, in which she plays Jenny’s dominant teacher. Martha and Jenny make love in front of the camera. The girls share good onscreen chemistry. Jenny’s first movie with Martha titled “Jenny eats Martha” gains 5 million views in one week!
Justin Sean: is a porn star. He is tall, balding and has a muscular body. He performs with Jenny in her second movie titled “Jenny Bubbles: bound and fucked!” Sean is rough with Jenny in the movie and causes her a lot of pain and humiliation. However, he has nothing personal against Jenny and is only doing his job.