Sissy Femboy Stories

6,661 results
Orientation
Length
Source
Infinite Scroll

Keeping My Sissy Secret

by VrijeVogel on Apr 24, 2019
Transgender & Crossdressers

YES! She really won't be home! I thought to myself as I cycled towards my house. My mother's car was missing from the driveway, meaning her plans for visiting a distant aunt hadn't been cancelled after all. Her wardrobe would be all mine for the entire weekend and I couldn't wait to try on her clothes. Aside from everyday clothes fit for a single mom, there...

Under Mommy's Direction Ch. 05

by MommysHypnoSissy on Apr 13, 2020
Transgender & Crossdressers

The rest of Jaime's day had been a whirlwind of tasks and chores to complete before his Mother got home. His online Sissy Trainer, who demanded that he refer to her as 'Mommy', had given him a myriad of tasks. First it was cleaning up his Mother's bed and sexy toys, putting everything back how he had found it. Then it was back to his room to dispose of his b...

The School Ch. 07

by NeighbourhoodSuccubus on Jan 15, 2019
Sci-Fi & Fantasy

Zamuel breathed hard against his captor's hand as she pushed him away from the heavy growls of guitars and loud lyrics he was too distracted to make sense of. She was powerful, toned and athletic compared to Zamuel's soft and meek form. He was helpless in her hands and could only continue walking under her firm guidance. They passed by a few femboys who too...

Feminizing First Step Ch. 07

by antares34 on Aug 24, 2020
Transgender & Crossdressers

I was meeting my internet "daddy" for the first time today. His last text message to me had been very clear: tie myself to the motel bed and wait for him to arrive. I stared at the antique bed with its black metal frame and headboard, wondering to myself if this was such a good idea. This rundown motel had been hard enough to find. I had never been to this...

Mom's Big Black Hobby Ch. 07

by MiddleKoala on Jul 13, 2020
Transgender & Crossdressers

This story has with homoerotic themes. If you are offended by such, do not read. This level of depravity is not to be taken lightly and the deeper down the rabbit hole you go the more you will find that may offend you. You have been warned! All characters in this story are over the age of 18. The entire story is fiction as are all characters. Any likeness a...

Glory-Filled Hole

by femboyslut on Sep 12, 2017
Transsexuals & Crossdressers

Ever since I was little, I always enjoyed dressing up in my sisters' clothes despite being a boy. This may have been because my dad left before I was born and so I had a big female influence due to my 3 elder sisters and my mum. When I was about 11, my sister Alice, 14, and my other sister Izzy, 16, decided to dress me up as a girl using all sorts of make-up...

Growth-XX

by FlatCap90210 on May 20, 2019
Science Fiction

James felt as if he was going insane. It was summer, the sun was shining and he was at the beach ogling girls. Tits of all shapes and sizes surrounded him, wrapped in bikini tops, one pieces and other pieces of fabric of varying coverage. James' heartbeat pounded in his ears and throbbed in his crotch, digging a furrow in the sand beneath him. He was lying o...

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The Birthday Party

by today_i_am26 on Jul 27, 2020
BDSM

Chapter 1 - The Negotiation We sat, the four of us, in a coffee shop on the high street. To the causal onlooker, we probably looked like university students meeting their parents for a catch up. The reality was something quite different. My Wife, Goddess, Dominant, Keyholder, had answered an online advert on my behalf; a couple looking for a Sissy to att...

Twice as Nice

by puzziboi on Mar 17, 2020
Transgender & Crossdressers

About ten Christmases ago, Lemar McCants had been shopping for gifts with his early tween daughter. On the list was his wife, his parents, and one of the middle school aged girl's classmates. He remembered the conversation. "Dad," Maryam beamed as she selected what appeared to be a tiny white rag doll with pink hair and a pink cat in the same box. "This is...

The School Ch. 04

by NeighbourhoodSuccubus on Mar 6, 2018
Sci-Fi & Fantasy

Editor's note: this story contains scenes of incest or incest content. ***** Zamuel woke up to the beeping of his morning alarm. Despite having a king-sized bed all to himself, he always woke up curled up and around Snugglebutt. This time a tad sticky in the crotch as his semen dribbled out of the toy once he softened and slipped out of it. It wasn't as d...