Playmate is a transgender romance novella written by Yu Sakurazawa.
Ten-year-old Derek has been more like an adoptive “sister” to Rupert Meadows, the young scion of a rich business family. It is customary for 11-year-old Rupert to dress Derek as a “bride” and playact being married to him. Disapproving of the two boys’ closeness and silly games, Rupert’s father sends Rupert away to a boarding school in Berkshire and, subsequently, to the US, far away from Derek. When the two guys meet as adults, sparks fly. Derek undergoes a sex change to please his lover. Derek is now known as Darlene.
Darlene and Rupert are very much in love until the burglary of Rupert’s mother’s expensive black pearls casts a shadow of suspicion on Darlene’s character and strains the relationship between her and Rupert.
Daryl/Darlene Peters: is a ten-year-old Anglo Indian boy, who has lost his whole family in an accident. He is teased by the Indian boys for his pale coloring and soft, effeminate mannerisms. Daryl has a beautiful feminine face and green eyes. Daryl’s life changes when he is adopted by the rich Meadows family and taken away to England. He gets good meals, an education and also grows close to his adoptive brother. Over the years, Daryl starts feeling that he is a woman trapped in a man’s body. He and his foster brother fall in love, after which Daryl undergoes a sex change. He is now called Darlene.
Rupert Meadows: is the arrogant, overbearing scion of a large business empire. He is tall, sun-tanned and has imperious brown eyes. He considers Daryl as a possession rather than a person. Rupert’s growing closeness to Daryl leads his father to send Rupert far away from home to complete his studies. Rupert returns home as a young man of 21. He is accompanied by his American girlfriend, Melanie, whom he wishes to introduce to his friends. Melanie breaks up with him abruptly, leaving Rupert in a bad state. Rupert subsequently coaxes the effeminate Daryl to dress up like a woman and accompany him to a party.
Rory Richards: is a 28-year-old felon who seeks refuge in Darlene’s house when pursued by the police. He has a boyish personality, has several tattoos and body piercings and dresses in baggy trousers and t-shirts. Rory works as a laborer but is also a minor thief. He rescues Darlene from the clutches of a rough, hardboiled pimp and provides her shelter in his home. Darlene discovers Rory to be a gem of a person, who is deeply interesting in knowing her likes, dislikes and opinions. Rory values Darlene as a person rather than as a possession.
Frank Meadows: is the father of Rupert/Daryl’s adoptive father. He is an Anglo Indian who runs a super successful chain of restaurants in Britain. He is mustached and wears expensive suits. He dictates the life of his son. Mr. Meadows disapproves of the closeness between Daryl and his son and sends Rupert far away from home to complete his studies. He expects Rupert to grow up to be a manly, hardboiled businessman and take over the family business empire ASAP. Frank Meadows doesn’t approve of the relationship between Rupert and Darlene. However, he accepts Darlene for the sake of his son’s health, happiness and progress.
Sheila Meadows: is Rupert’s mother/Daryl’s adoptive mother. She is a petite lady, who wears expensive clothes and jewelry. When her necklace of black pearls is stolen, Mrs. Meadows suspects Darlene of theft. She behaves in a rude and accusatory manner, which breaks Darlene’s heart and leads her to leave Meadows Mansion. Later on, Mrs. Meadows accepts Darlene as her son’s bride-to-be and even gifts her the necklace of black pearls, which has been recovered from the real thief.
Edwin Brown: is a childhood friend of Rupert’s. He is a very fair young man. When Rupert returns from England, Edwin throws a party in his honor. Daryl accompanies Rupert to Edwin’s party, wearing women’s clothes and pretending to be Rupert’s girlfriend.
Melanie: is Rupert’s American girlfriend. She is a beautiful, temperamental girl who isn’t sure of her feelings towards Rupert. Yet she accompanies him to England only to realize that she is in love with someone else. She subsequently returns to the US, leaving Rupert in a bad state.
Sister Martha: is one of the nuns who run the church-affiliated orphanage Daryl is sent to after he loses his family. Sister Martha consoles Daryl whenever he misses his family. She tells him that those who don’t have a soul in the world have God. When the Meadows come to the orphanage to adopt Daryl, Sister Martha helps him get dressed.