Femboys Stories

42 results
Orientation
Length
Source
Infinite Scroll

The Devlin Family

by grimbous on Jul 25, 2020
Fantasy

Readers of mine will recognize similarities to my other story Runt of the Litter. The set up is the same, clueless young man is let in on a family secret and then the fun begins, but in this one I wanted to dabble more with teratophilia and experiment with the storytelling options of having magic to play with. Beyond this you can expect my usual bullshit. Na...

Open in Reader

My Cleaner

by gendidi on Sep 13, 2017
Transsexuals & Crossdressers

I'm a 40 years old married man. My wife is much older and we stopped having sex a few year ago. We spend a few months a year in our homes in UK and Malaysia. I have never had experience with a ladyboy my whole life. Just not my cup of tea. We went to LOS a few times and saw ladyboys on the street but nothing happened. Due to my looks, I did attract some femb...

House Rules Ch. 09

by EROTICbearscribe on Jan 22, 2020
Transgender & Crossdressers

AUTHOR'S NOTE: This story contains characters and references to events in two previous stories I have written: Just Across The Hall and PIXIE: Sissy Stripper. It is not necessary to have read these two story chains. This chapter of House Rules could stand on its own for entertainment purposes. If, however you want context, please read the other two stories f...

Unleashed

by puzziboi on Sep 16, 2017
Transsexuals & Crossdressers

Ray stood up from the chair in the New Millennium African Braiding salon and checked his fresh cornrows in the lengthy wall mirror. He folded off three twenty dollar bills and told the attractive dark-skinned stylist from Ghana to keep the change. She had attempted on occasion to get the six-foot-four-inch, two hundred forty pound brother to get inside her p...

Bulging Underwear

by Knicker_lover on Dec 9, 2019
First Time

The reason I had met up with Adam was because the previous month I had come across his profile after seeing he had shared some bulging panty pictures on a well known porn site. It was one of those mornings where I was in the mood to masturbate whilst looking at some young guy in women's underwear. As it was, I ended up wanking over his profile picture which...

Wealthy Sissy Surrender Station

by AmberFemXD on Sep 16, 2017
Transsexuals & Crossdressers

Fire immediately engulfed the house just next door after an earth shaking explosion rocked the neighborhood. Fear was setting in. The rebels were getting closer and closer, Inch by inch. Relentlessly. Terror crept in as silhouettes and shadows extended deeper into the darkness with sudden flashes of light exposing their footsteps. I held my breath and cowere...

Training Carter

by XtinaSmith2017 on Aug 7, 2018
Transsexuals & Crossdressers

"Come on baby, you're ready for this, you got this..." Emma urged, her hands resting on his smooth slender thighs, caressing and squeezing eagerly as she lay on her back, looking up at the boy, her boyfriend, who leaned back lithely, one of his hands resting on her own thicker thigh for support as his other hand gripped her steely lubricated length, guiding...

Neighbors Sissy Son

by newfield1981 on Sep 18, 2017
Transsexuals & Crossdressers

About two months ago a woman and her son moved into the vacant apartment next to mine. I noticed right away how effeminate the son was, even though he was dressed like any other 18yr old boy, he couldn't have weighed more than 115lbs and his facial features were soft and delicate! Having a thing for femboys (twinks) I set my sights on this one! Since I wor...

Blurpees Before Lights Out

by puzziboi on Jun 1, 2020
Transgender & Crossdressers

The scrawny, balding man with a pointy nose and large ears cleared his throat. He was seated up on the dais wearing his black robe. He spoke in a low tone. "Will the jury foreperson please stand," he half asked, half instructed. A bronze-skinned woman wearing too many bangles and a lot of bright purple hair weave stood. The judge inquired, "Has the jury re...

Izzy and Emily Ch. 01: Two Redheads

by inkstand on Oct 31, 2018
Transgender & Crossdressers

The thump and boom of music filled the darkly lit club. I could feel its pulse thunder in my chest. The sea of dancing bodies writhed and bobbed to the tempo. The crowd, stocked with painted femboys such as myself, crossdressers and those who straddled sexuality as neither boy nor girl but an amalgamation of both, moved as a single mass. I had joined the de...