Category: Sissy Stories

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

    Just like many young teenage boys my body was growing taller, but it was still as thin as a twig.  Unlike many teens I was not into organized sports.  I was more of a loner and liked to ride my racing bike after school.  I wore tight fitting colorful spandex shorts and jerseys.  … Continue reading The Bicycle Ride

Just Trying to Please — by jessicablank Brad carefully brushed the mascara up… up… up his eyelashes, struggling not to squint at his own reflection in the mirror. The eye shadow was a perfect shade of plumb, the brows exactingly tweezed and arched. And the eyes that stared back into his were so feminine and … Continue reading Just Trying to Please