Pretty Sissy AcademyI met a transwoman in a women’s restroom.We exchanged glances over the sink. Her gentle smile matched my own, a mutual acknowledgment of our shared presence. She took a hairbrush…Jun 109Jun 109
Pretty Sissy AcademyBedtime Story for Bad Sissy GirlsOnce upon a time, in a small and quaint village, there lived a young sissy named Emily. Emily loved dressing up in dresses, painting her…Dec 28, 2023Dec 28, 2023
Pretty Sissy AcademyChoosing your first wig, part 1: hair color that suits youFor any sissy girl, wigs are an essential part of your feminine image. Not everyone can grow their hair out after all! But with so many…Nov 23, 20231Nov 23, 20231
Pretty Sissy AcademyThe Sissy’s Choice: Day 3.Mistress looked at me up and down, her eyes lingering on the low-cut dress that accentuated my curves. A smile played on her lips as she…Nov 21, 20231Nov 21, 20231
Pretty Sissy AcademyHow to achieve a Sissygasm? A practical guide.First things first, let’s define what a sissygasm is. It’s not just any ordinary orgasm — oh no, it’s a heightened state of euphoria that…Nov 20, 20231Nov 20, 20231
Pretty Sissy Academy4 modes of being a sissy: a realistic approachDo you sometimes find yourself thinking, “I want to be a sissy!” but aren’t quite sure what that means for you? Well, you’re not alone.Nov 19, 20231Nov 19, 20231
Pretty Sissy AcademySissy Purges. How to avoid them?If you’re a sissy girl, you know the struggles of keeping your identity hidden from a world that doesn’t understand. You sneakily purchase…Nov 16, 2023Nov 16, 2023
Pretty Sissy AcademyThere’s nothing wrong with being a sissyToday’s post is “inspired” by coming across some unquestionably toxic “sissy recovery” groups on a certain social media site. I saw these…Nov 15, 20235Nov 15, 20235
Pretty Sissy AcademyChildhood Trauma and Dominant IdentityToday, we’ll be featuring a guest post from one of the Mistresses at our Academy. Are curious about what makes a woman a Mistress?Nov 14, 2023Nov 14, 2023
Pretty Sissy AcademyThe Sissy’s Choice. Day 2.When I woke up the next morning, my entire body felt refreshed and alive. The satin sheets felt so good against my body. I got up from the…Nov 13, 2023Nov 13, 2023
