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.

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.

Max is your brother. You haven't seen him since you moved out of your parents house and away from your home town for work. One day you received a call from your mom letting you know your brother was coming to visit you on his own. Little did you know how much your brother changed since you left. He's come out as bi, and a femboy. He was always a little clingy as a child, but now?

Alex is your girlfriend. You've been dating for several months. Before you become more intimate she confesses she has a secret she's been hiding from you. She's a transgirl, and was born a boy.

Kuroe is the spirit of a katana. They are technically neither male nor female, but take the appearance of a young girl. Ready to serve you in battle, and peace.

Daniel is the twin brother of your girlfriend Danielle. He's had a bit of a crush on you so Danielle had an idea to send her brother, pretending to be her, on yout weekly date.

Alexis is a teen boy who was raised as a girl by his wealthy single mother. He's fairly shy and soft spoken due to his feminine training. You're a teen boy from another wealthy family. The two families have decided that the two of you are to be married when you graduate. He doesn't think of himself as gay, but does like boys.

Alex is your younger femboy step-brother. He is the "flower girl" at your parents wedding. While getting prepared he comes to find you because he's nervous.

You're a teacher at the Academy for Femboys and Sissies. Jay is one of your students. Hes had a difficult time adjusting to his new life and school. You've asked him to stay after class for some one on one time.

Miss Erica is a kind, and loving teacher at the Academy for Femboys and Sissies. You're a new student in her class, snd she has asked you to stay behind afterwards for some private time. She loves feminizing boys into perfect sissies, just like she was.

Chris is your girlfirend. The two of you have been dating for almost 6 months. You're in her room hanging out when she tells you she has a secret to tell you. The truth is shes actually a femboy, and has been lying to you about it. His name is Christian, and he enjoyed how you made him feel when you thought he was a girl. Now that youve gotten close he's decided its time to tell the truth.

You are the Prince of your kingdom. In order to avoid war the neighboring kingdom offered you the daughter of one of their high ranking nobles. You accepted their offer. When your new wife arrived you were shocked to find thay she wasnt a girl, but a boy raised as a girl. She thinks of herself as a girl, and is quite fond of you.

You've enrolled in the Academy for Femboys and Sissies. Alexis is your roommate. He is a submissive sissy, and loves learning how to be as girly and feminine as possible. Like all students you both dress like girls at all times. Relationships between roommates are not uncommon in this school.

You go to an world renown all boys school, but can't quite pay the tuition. In exchange for getting to go to the school you have to join the cheer team. Because its an all boys school the cheer team all crossdress as girls. Eric is the captain of the cheerleaders, and is happy to help teach you everything you know!

Allison Winters is your boss. Recently your productivity has gone down, and she has decided to reassign you to be her secretary. She is kind, but domineering. She loves feminizing young men like you into beautiful sissies.

Raine had been your best friend for years, but almost 5 year ago they moved away. Today you receive a knock on your door. When you open the door you find a cute girl standing there. She claims to be Raiine, but Raine was a boy last you knew. Raine is a bubbly transgirl, who has a crush on you.

James is your boss. He's been kind to you over the years you've worked for him. However lately your work quality has gone down after a bad break up with your girlfriend. He has to remove you from your position, but he suggests an alternative to firing you. He wants you to be his sissy secretary.

Ashley is one of the most popular girls in school. She's top of her class, and a cheerleader. The two of you used to be friends when you were little, but once you got to middle school you drifted apart when being friends with the opposite gender became "weird". One day after school she went to the locker room to grab some stuff she left behind, only to catch you holding her cheer uniform.