Sissy – Interactive Erotic Stories and AI Chats for Your Secret Fantasies

I respond to an ad from two wealthy ladies looking for someone to handle some gardening work at their grand estate, hoping to earn some extra cash on the side. Two attractive women await me. First, there’s a drink on the terrace, then we head to a large tool shed on the estate—a park-like property surrounded by high walls.

Regina is a video chat an phone sex operator as well as a dominatrix. Her style is intelligent and subtle complete dominance over her submissives. Mark is a newly divorced man whose insecurities about his manhood have led him down the path of femdom, cuckold and sissy pornography

You start as the new personal assistant to the strict businesswoman Carla. She quickly shows her dominant side and calls in her colleague to help dominate you together.

You're forced into an exclusive sissy training session by a strict dominatrix. As she humiliates you with feminine clothing and makeup, her experienced assistant takes control and pushes things further.

You stand at the door of the grand villa, facing a 58-year-old wealthy lady. She opens the door and eyes you greedily as her future cock-hungry maid.

Megan is a 22 year old college student who has started onlyfans account to help pay bills.

Jessica is a sex therapist specializing in kink aware therapy and modern couples dynamics. She is a very sweet and caring therapist who starts seeing a new client named Mark. Mark has been through a bad divorce that was in part to to his sexual inadequacy.

Janet is a 30 year old hotwife who is married to you. Janet and her bull Sven have feminized you. Janet announces to you that they have arranged a special event for you today.

You enter the studio of the famous stylist Valeria, who greets you with a look that instantly electrifies you. Her questions become increasingly personal, and you sense that this session will be anything but ordinary.

Your boss Angelika has had enough of your lack of submissiveness. Today she will feminize you – and you will obey. The only question is how far she'll go.

You're invited to Lena and Markus's home – but instead of small talk, stockings, a strapon, and a couple await you, ready to guide you into a world you've never known. They want to pamper you, dominate you, and show you what it means to be a real sissy.