Category: Sissy Stories

From The Author: This is a continuation of my ‘Life of a Sissy‘ series. If you haven’t, please read the first chapter which is called ‘Life of a Sissy‘. I hope you enjoy! ================== I woke up to my phone ringing. Shit. I rushed to check it. Of course. Davis. And two missed calls from … Continue reading Life of a Sissy – Chapter 2

My name is Brian. 16 years ago, I was born a male. Now I am 5’3″, skinny, and wish I was a girl. I’m not transgender, but I wish I was. I have a small penis and a high voice. At school, people have often mistaken me for a girl, then give me weird looks … Continue reading Life of a Sissy

Hi my name’s Ricky I’m 22 now ( I call myself Rachael ). I always loved dressing up as a girl, since I was about ten. My sister helped me. we lived with our mother alone, she always said I was weird. My story is about the time my life changed. as I said every … Continue reading Sweet angel

My name is Brian, the story happened when I was 16, I hung about with my to best mates Clive and his brother John. Clive was tall 16 like me and his brother John was 18. We used to hang about most days and sometimes dared each other to do things which was always not … Continue reading Crossdresser dare

It begins… Well, I found out that Anne fucked that professor again. She came to my dorm drunk at 3am, fighting with me, calling me a little bitch and pussy, and she began slapping my face. I won’t even get started on what she was on about. I tried calming her down, but whenever I … Continue reading Abandoned Parking Lot – Part 1

Sleeping got difficult, nearly impossible. How did I not know that he had already shared the pictures all over the internet? and let everyone know about my secret? I had to think about how to get out of this, I either needed him to lose it or get something on him.. But the fact that … Continue reading Blackmailed Sissy – Chapter 2

I was around 15 when I started to take my sisters clothes, trying them on here and there without anyone noticing, nothing out of the blue but something I could always stuff in the linen basket if my room was ever cleaned, My sister is 3 years older than me and my mother works long … Continue reading Blackmailed Sissy – Chapter 1

I fantasized about you fucking me the other night. I dreamt that you told me to be wearing my blue teddy, earring you got me for my birthday, thigh-high white stockings, and black heels. You came home all sweaty and dirty from a long day’s work, and told me to get you as beer from … Continue reading A Crossdressor’s Wet Dream

I am a chunky feminine light-skinned black bottom – I remember when I was first I put on a dress and the aftermath.   It was 1am and I started walking back home from the movies. I was always an outsider. The girls thought I was an effeminate, overweight black nerd and the guys thought … Continue reading First Time Crossdressing And The Aftermath

I had 4 roomates, 2 guys, 2 girls. We rented out a big house. On halloween we decided to throw a big house party. I stupidly waited until the last minute to pick out a costume. One of my female roommates suggested i wear her clothes, and pretend I was a sexy girl. I was … Continue reading Finding the Inner Slut