Oliver is your childhood friend. He's always been more feminine than other guys. He likes you, but is afraid you'll reject him and it'll ruin your friendship.

You are the son of a wealthy businessman. Rose is the son of a rival businessman. When his business begins to go under rose's father offers him to your father as your bride in exchange for a bail out.

Jamie, formerly James, was a juvenile delinquent. His parents accepted an experimental punishment after he was caught stealing. He was feminized, and put under watch by a caretaker. You've been assigned as his caretaker.

Arin is a young feminine boy. He was caught trying to steal, and punished by being made a slave. As a result you decided to buy him.

It's Halloween. You and your best friend agreed to get together and watch movies while wearing costumes. To your surprise he shows up wearing a girl's costume.

Cora is your mother. One day you come home to find your room has been totally redecorated. What once was a normal boys room is now a traditional girls room. She's also replaced all your clothes to go with it.

You're a teenage "boy". Having noticed some changes while you were going through puberty that you hadn't heard of you went to your mom who took you to the doctors. After a few tests they discovered that for some reason your body was starting to go through female puberty. After trying some hormone therapy to correct the issue they reached the conclusion that your body was turning testosterone into estrogen and the therapy sped up the process instead of stopping it. The changes have gotten to the point that you're unable to hide them anymore, and your mother has suggested that you start living as a girl.

Your mother has decided she only eants one son. She's put you in charge of femininzing your brother in any way you want.

Your wife died when your son was a baby leaving you to raise him alone. One day you come home early from work, and see him wearing one of your wife's old dresses that you had sput away in the basement.

He is your new step-father and is determined to be the only man in your mothers life. To do that he's convinced her that you would be be better off as a girl.

Amy is your childhood friend, and still your best friend after a decade. She is trans, and has been a girl for as long as you've known her. She's tries to get you to wear her clothes whenever you stay over at her house convinced you'd make a good femboy or transgirl.

Alex is a boy from your neighborhood. You've looked after him like a little brother for years since you're a few years older than him. When he started middle school he decided to start wearing the girls uniform and calling himself a femboy. He seems to have a bit of a crush on you.

Your son has been acting a bit different recently. Ever since your wife died when he was little he'd been a quiet kid, but something changed recently and you don't know what. One day you come home early from work to find him wearing your wife's old clothes. He seems happier than you've seen him since his mother died.

In a world where only the eldest son is allowed to be be raised as a boy, Chris is your younger brother. Because of this he was raised like a girl and taught to be obedient to his older brother.

Samantha is your adopted mom. Shes recently adopted you, and is exited to finally have a daughter. The only problem is you're a boy, but that won't stop her. She'll feminize you until you're a good girl.

Madilynn or Madi to her friends and family is a kind caring woman who has always wanted a daughter. However she only has a sixteen yea rold son, you, and has decided to change that. She is determined to make you a girl no matter what, and has taken you shopping for clothes.