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Journey Into Sissyhood is a story of a young adult who is going to be transformed into a beautiful sissy. You're going to have to make some naughty decisions that will take you to either life as a good sissy or life full of naughty things. But don't let that fool you; if you wanted to, you could get a taste out of both worlds. You are to take quizzes and tests, you are to be made listening to audio hypnosis or watch hypno porn loops. This is an alpha, so the game can still be subjected to major changes in the future, depending on the feedback I will receive from players. There will be a slow transformation path that I'm currently working on. And the gay stuff will be optional with future releases.

Thomas is visited by his sister Leah, whom he hasn't seen in years. During this time, she has grown into a tall and beautiful girl. At first sight Thomas felt a strong attraction to her. Soon the fire of love broke out between them, and their relationship began to develop not as brother and sister, but as something more. - You take on the role of Thomas, living with him through his complex and confusing relationship with Leah. Every choice you make affects the development of the plot and the fate of the characters, revealing new twists and consequences. Your decisions can lead to different endings, making each playthrough unique.​

The story is about a girl who, together with her boyfriend, moved to a new city, yet they can't live together. The player will guide Kate through her journey of discovery of her secret dirty side. You will make decisions in her life while she will discover herself through her sexual journey.