Sissy Brother Stories

49,708 results
Orientation
Length
Source
Infinite Scroll

Simran Khalsa of Punjab

by Samuelx on Jan 14, 2018
Interracial Love

The sun rose over the City of Johannesburg in the Gauteng region, bathing one of South Africa's most beautiful places in its golden light. Johannesburg, a world-class city which emerged on the world stage almost a decade ago during the World Cup, is home to a diverse population. Zulus, Xhosas, Germans, Dutchmen, Englishmen, Chinese, Indians, all make their h...

A Sissy Story

by PinkRebecca on Feb 21, 2020
Fetish

You always were a normal boy growing up, weren't you? Played some sports, although not to an extent where you stood out anywhere or made any teams. You had a normal friend group, as far as you knew atleast. You liked girls, like most of the boys around you, although you lacked the curage to talk to them. Well not to talk to girls in general but in a romantic...

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The Farm Ch. 03

by Stillherer on Sep 16, 2017
Transsexuals & Crossdressers

Ed took his time with me. He constantly taunted the two younger men as they waited eagerly for their turn to stuff their hard cocks into my cum filled sissy cunt. "Only right that your daddy gave his bitch to a real man before you two pathetic losers." After smothering me with his fat sweaty gut and smelly cock Ed had swapped ends never letting go of his pri...

I Love Men to wear my Satin Panties Pt. 01

by Manndee on Apr 25, 2018
Transsexuals & Crossdressers

I was a quiet unassuming lad from the East end of London; I was 22 years old when I left home, it followed a number of pure flukes that all happened back to back, because of this I had had an amazing start to my life in my first job as a City trader. Unfortunately, things at home with my girlfriend were getting difficult after me losing my job. It was now 4...

Black Lady Cuckolding Black Men

by Samuelx on Sep 17, 2017
BDSM

What's up dear family? My name is Yasmina Hussein and I'm a Somali Canadian woman living in the City of Ottawa, Ontario. A while ago I discovered the world of BDSM, shortly after my divorce, and have been really into it ever since. I discovered that I have a talent for and a desire to dominate people, especially men of color. As a Somali Canadian woman, I wa...

Older Sister's Nylons Ch. 01

by BlkNYLONS on Sep 18, 2017
Fetish

This took place in 1966. A time when the fashion called for women too wear girdles, garters, and shiny ultra sheer reinforced heel and toe nylons, spiked heel pumps/mules daily! A time when my fetish for nylons was young and in full bloom! You little pervert! I jumped up, dropped the high heel pump in my hand that I had held over my nose and I turned around...

Sissy and His Sister

by secondsamuel on Aug 28, 2018
Transsexuals & Crossdressers

Author's note: I am recovering from repeated surgeries on both arms to correct a degenerative nerve condition. To write this, I am using a voice to text software which isn't always as accurate as I would like it to be. As my recovery time will take more than a year, I have decided to continue writing and give my best effort at doing the thing I love. Please,...

A Missy Affair

by Stillherer on Sep 16, 2017
Transsexuals & Crossdressers

I knew I was being careful. I thought I was being clever. But I never thought I could be caught in such incriminating circumstances by of all people my sister-in-laws husbands parents. I was playing the good brother-in-law by doing a bunch of minor home reno's for my wife's sister and her husband. To my delight they trusted me implicitly and left me alone in...

Black Cross Dresser Chronicles

by Samuelx on Sep 16, 2017
Transsexuals & Crossdressers

What's up people? My government name is Omar Woodson but you may call Madame Orillia. The Black Canadian cross-dressing diva extraordinaire of metropolitan Toronto, Ontario. One of a few outspoken Black cross-dressers in town, and definitely one of the most wickedly fun and entertaining. Lots of Black men like to wear wigs, skirts, nylon panty hoses, bras an...

Sissy Maid Son Pt. 03

by Robyn228 on Oct 21, 2019
Transgender & Crossdressers

Note: This story is entirely a work of fiction, and should only be viewed as a fantasy. Any similarities to actual events or people are entirely coincidental. All characters are over 18. ***** Peter stood there looking at the black stilettos, with so many questions on his mind. He wondered why his brother would ever own stilettos, much less why their mothe...