I saw someone begin a "diary" of their experiences as a sissy on here recently and it inspired me to give it a shot myself. The following will be true stories from my past starting from the first time I ever hooked up with a Tranny / Cross dresser / Sissy. First things first, I consider myself to be a straight male; despite having had sex with all of the a...
Part 1 - The young man Barry was in his early fifties. He stood about 6ft-1, and weighed nearly 300 pounds. He had brown hair going to gray, and green eyes. In his youth, he'd been considered handsome. Barry was also very lonely. He was struggling to cope after the loss of his wife nearly five years ago. His wife of 25 years was a companion he sorely misse...
*** Stories with transgender themes which I hope will be of interest to those who like women, or would like to be a woman. Which includes me! *** It all really started on a Monday. One bright sunny Monday, early summer, an unusually warm day for June in England. And it really was stupid thing to do. Sun-bathing in a bikini in my back garden, that is. I'd o...
In the eyes of the world, I am many things. She-male. Tranny. Chick with dick. Those are the names they've got for me. What do I call myself? I call myself Angela Shay. Anyone looking at me would see a five-foot-nine, curvy Black woman in her mid-thirties with a nice rack, wide hips and a big round ass. I hate the terms she-male, tranny and chick with dick,...
I grew up out in the country as a boy with my mother and 2 sisters. My dad was never around since he was always off working or as we found out some years later running around cheating. If we saw him at all it was on the weekends for a quick family outing to the mountains or park. Once in a while mom and dad would get all dressed up and go out to dinner. This...
The ruby glowed in the stores fluorescent lights of the old thrift shop, shooting beams of red against the countertop as James walked by. The glint of light catching his eye as he passed, drawn into its radiance he reached out and gasped at it. "Excuse me?" he asked the woman texting behind the counter, "How much is this?" The girl unenthused by her annoyi...
This was inspired by a fan, Pantycladlad. He said he liked cross-dresser stories with some rough treatment. So be warned, there is some non-consent action and a little bit of roughess. Like always, I did it all myself, and although I proofread, there may be a few things I missed. There will be some Midwest regionalisms too. I hope none of it stops you from e...
Since my first story, I have developed into a real estim freak. My daily pleasures are such that my body almost 'knows' that it is time. I generally masturbate every morning anyway, but estim is almost always the usual method. I have taken to looking at online porn the whole time as I stimulate myself for at least an hour daily. The sensations are so exqui...
Chapter Five: Monday Morning You look so Fine. About 7:00am and I awake from the sofa bed of Gillian's place. I feel better after sleeping off the fun Sunday night activities with Kerri and friends. I need to wash up and get home to dress for my Monday schedule at my dominatrix studio. I shower and feel refreshed. As I dry off, there is a door knock and Ker...
He and I know each other very well, though we live in separate states. I shared a rape fantasy with him that was to happen when he came to visit me. Instead, he caught me off guard when I visited him and he raped me. I fought and fought but he had more strength and he raped my pussy and raped my ass and left me bruised and bleeding. We share many fantasies...