Crossdressing Brother Stories

45,080 results
Orientation
Length
Source
Infinite Scroll

Blood of the Clans Ch. 48

by RoyceConnors on Sep 18, 2017
Novels and Novellas

The arrows left their bow strings, the whistling only lasting a second or two, before more screams echoed off the hills around them. Two more men stood without their manhood, while the third was pierced in his abdomen. The two men stood back and watched, as Glendon's last archer, Callum McInnis took aim once more. All the men watched in suspense, Callum's sh...

Into the Vampire's Lair Ch. 07

by ArtForm on Sep 26, 2017
NonHuman

NB: Credit goes to my editor, wildheartedangel for her efficient and constructive work as always. =) To my readers, thank you for your comments from the last chapter! I have taken some of them into consideration and hopefully I've managed to address some of the questions too in this chapter. However, we're going to focus a bit more on Alaron and Erika in th...

The Devil in Hannah Prynne

by JulianDelacourt on Oct 8, 2019
First Time

This story is an entry in the Summer Lovin 2019 contest. Please vote. Thanks and enjoy! No one has to tell me how badly I fucked up. On the second night home of my summer vacation from university, I go to a house party with my best friend in high school, Darby, get wasted, and throw up on my front yard where my mom finds me curled up asleep at 6:30 in the m...

Sister's Shemale Friend

by silkstockingslover on Sep 12, 2018
Illustrated

Sister's Shemale Friend Summary: Family seduced and dominated by an irresistible shemale. Note 1: This is a Summer 2018 Contest Story so please vote. Note 2: Thanks to DarkBreezly for creating the pictures in this story. Note 3: Thanks to Tex Beethoven, Robert and Wayne for editing this story. I came home from work a couple hours early, as our manager...

Andrea Millhouse Pt. 04

by ThickAsThieves on Jul 29, 2019
Romance

_________ 6 __________ I was vaguely aware of distant engine noise and Andrea's presence as she began moving around in the darkness, shaking the mattress as she did so. Suddenly, high pitched air horns ripped through the stillness of the night as several massive diesels thundered closely by, shaking Long Grey Cloud and rocking the mattress which Andrea and...

Within Pt. 06

by Alexis_Green_writes on Dec 12, 2018
NonHuman

The next morning Isabelle was up before dawn. She slid from Alasdair's arms as quietly as she could and padded to the washroom. When she came out a few minutes later the doors to the balcony were open and Alasdair was outside. She went out to join him in the cool morning air. "Did I wake you?" she asked softly. He reached out to take her hand and pulled her...

Twin Set

by thrillerauthor on Mar 11, 2019
Transgender & Crossdressers

"Set point!" My twin sister stuck out her tongue as she crept in front of the baseline. We had played against each other countless times, and it always seemed to come down to this, a long deuce or a tiebreaker at the end of a tense, competitive match. Although I was a boy and she was a girl, we were evenly matched, and I sometimes felt that the only edge I...

Better as Emmy Ch. 01-05

by cactusaur on Jun 8, 2020
Transgender & Crossdressers

Hi everyone! It's been a while since I've posted any new stories here, but a fan reached out for a continuation and cross-over of the Emmy's New Kinks and Better as Riley stories. This new story builds on the characters, themes, and storylines from Emmy's New Kinks and Better as Riley. I recommend reading those before diving in here. Themes: Feminization, t...

Pink Love in Pink City

by Johny3727 on Jun 9, 2020
Group Sex

This is a narrative of erotic encounter that I had in my 20s in a small, North Indian town of Jaipur also known as Pink City hence the title. I have changed names but everything is pretty close to my recollection and truth. I have never written anything before so please be patient and enjoy! Just a year ago I had completed my M.B.A. and landed at a global c...

The New Programmer

by JupiterMars on Mar 10, 2020
Romance

The new programmer sat at the workstation next to Sharon's. He was already plugged in and working when she arrived that morning. His back was to her so she couldn't see his face, but she could tell that he was tall, lean, and also apparently having a frustrating first day. Fanex was a division of Rotect, a large software, and tech company. Fanex wrote code...