Crossdress Brother Stories

44,291 results
Orientation
Length
Source
Infinite Scroll

Biker Bitch Ch. 01

by MicheleNylons on Dec 21, 2017
Transsexuals & Crossdressers

Chapter One: Cassie Cassie woke up feeling hungover, hungry, thirsty, beaten and abused. She was still chained to the billiard table in the Beasts of Burden Motorcycle Club clubhouse. She rubbed her ankle where the chain was manacled to her leg. Her nylon stocking had worn through and her skin was red and bleeding. Had it really been four days? Cassie s...

A Wife A Little To Understanding

by felicia_rene on Oct 12, 2020
Transgender & Crossdressers

Present day: We arrived at the 'Sissy Salon' which was a covert sex club for downlow gay wealthy men and lesbians. As his agent and pimp I collected all his performance fees. I walked into the 'Sissy Salon' to make sure that everything was in place so my sissy husband could perform. Then I went to his dressing room to make sure everything I requested for me...

Being Sarah

by Alex_Lockheed on Sep 25, 2017
Transsexuals & Crossdressers

Please note, this is a story about a male-to-female crossdresser. It includes themes of bisexuality, dominance/submission, embarrassing erections, anal play, cunnilingus and cum-eating. If you like that, awesome. If you don't maybe it's time to check another post. You can't say I haven't warned you ;) **** There are many difficult decisions I've had to ma...

A Dress Up Party with the Girls

by bigrusker on Sep 12, 2017
Group Sex

I stood there in the mirror, contemplating what I was about it do. Do you have what it takes to do this? I asked myself. At this point, it didn't really matter. I could hear the four giggling girls downstairs and despite only having arrived a few minutes ago I knew they had started the party quite a while ago and had already had a fair amount of wine. But t...

Inaugural Crossdress Sexfight Ch. 04

by danidhotcd on Sep 16, 2017
Transsexuals & Crossdressers

The league's first tag team match featuring another newbie. Participants Dani Davis (me): Record 1-3 Jamie Play: Record 1-0 vs Dani Delights: Record 1-1 Mandy Spencer: Record 0-0 After hearing about our club, I was approached by a new gurl, Mandy, who had the body to fit right into our league. She was a rookie, but was interested in a tag team match after...

The Awakening Ch. 01

by MicheleNylons on Sep 13, 2017
Transsexuals & Crossdressers

Part One -- The Woman In The Mirror Dark; then light; my eyelids flutter. "Can he hear us?" a woman's voice. Dark; then light. "He's still comatose; but he's improving," an authoritative male voice. Light; now dark, the dream returns. I'm inside the mirror but I can't be seen. I try to reach through the glass but I can't. I try to speak but I am mute....

Kasey's Confession Ch. 14

by KaseyLegs on Sep 14, 2017
Transsexuals & Crossdressers

Lying in the hospital bed, hooked up to monitors and who knows what else, I just stared out in shock. It was to be expected, they said, as they explained I had been in a coma for a very long time. What they did not know was that the source of my confusion ran much deeper than just waking up disoriented after a long time "away." I had absolutely no idea who...

Hostess with the Mostest Ch. 10

by MicheleNylons on Sep 15, 2017
Transsexuals & Crossdressers

Chapter Ten -- The Hostess With The Mostest "I don't care if there's a fucking flying saucer from Mars down there; I just want some sleep," Candi replied and Millie giggled as the Skyliner made its approach into Changi airport, Singapore. The flight deck crew and the first class hostesses were rushed through customs and immigration and bussed away to a fiv...

The Agreement

by komrad1156 on Sep 18, 2017
Transsexuals & Crossdressers

Author's note: I prefer to write in the third person as it gives the writer so much more flexibility. However, I've written this story in the first person for one reason—it is my own personal story with love, marriage, crossdressing, and the ups and downs it invariably brings to a relationship. My name is David Calvin Peterson. My friends call me Cal. A smal...

Sissy Perfection

by cornthuxton on Dec 23, 2019
Transgender & Crossdressers

Hello. I had done just about everything there was to do mature, lesbians, trannies. And several times each variety. So I thought it was time for a twink. As with my previous adventures Hong Kong was my hunting ground. Two, week long trips a year made it easy for me to indulge me desires. I guess I am pan sexual...whatever that means. I'm open to lots of...