Sissy Brother Stories

49,708 results
Orientation
Length
Source
Infinite Scroll

Just the Way You Are

by Sandwiches_Are_Good_Too on Sep 16, 2017
Transsexuals & Crossdressers

"No! You are not taking my babies from me!" "This isn't about you! Its about providing my sons with the best home environment, and that's not with the woman who may be high as a kite at any given moment!" "If you had paid an ounce of attention to anything that was going on in your 'home environment,' you would have noticed that I've been clean for twelve...

Whore for Succubus Ch. 02

by Mixedwritings1993 on Sep 13, 2017
Sci-Fi & Fantasy

David woke up at around 8 o' clock in the morning. He was feeling really numb and half dead to begin with. He wondered what dream-like state he was in as he tried to differentiate between his trance and reality. Both of them seemed identical, except for the presence of a specter-like, bizarre woman. His hands were holding his penis lightly and he felt the od...

Cuckbitch Pt. 01: Confession

by Satin_Dani on Jun 19, 2019
Fetish

"Good morning bitch," the text message woke me up. "Have as much fun as I did last night?" It was almost a rhetorical question, although I did have fun. Lucy is a senior officer in the Army. We met years ago in our formative years when I was still in the military. We became good friends and maintained the relationship over the years. We were like best buds:...

What Just Happened? Ch. 02

by annie_00 on Sep 12, 2017
Transsexuals & Crossdressers

02 – Am I a pervert? When we got home it was late in the afternoon. We had been gone all day, first to the salon, then shopping, lunch, drinks and the crossdresser store. I was tired but felt very sexy under my clothes. I did not want Beth, my step sister, to know that I totally enjoyed the experience today. I thought that she would think I am perverted. A...

Sissy for Mommy's Nipple Cream Ch. 05

by ppeaks42 on Nov 2, 2020
Transgender & Crossdressers

The evening after Jaime's doomed attempt at seducing Julia found the young sissy crying into her pillow as she tried to reconcile herself to the whirlwind of changes she'd gone through. Less than two months ago "Jaime" had been nothing but a shared figment of imagination, a character he dressed as for his regular breastfeedings with his mother. When he'd tri...

Ash's New Career Pt. 02

by Fibaro on Sep 28, 2020
Transgender & Crossdressers

Standing back in the doorway of her own room Keira was surprised to see the wonderful job Ash had done with his makeup. It looked nearly as good as her own best effort despite the colours she had given him. She smiled watching how Ash applied the last touches to his makeup look before coughing loudly just when he was putting the brush down. Ash who had bee...

Black Man Becomes A Sissy Maid

by Samuelx on Sep 16, 2017
Transsexuals & Crossdressers

My name is Anderson James Crawford. I'm a big and tall young Black man living in the City of Ottawa, Province of Ontario. I presently attend Carleton University, where I'm studying Criminal Law. I originally hail from the City of Atlanta, Georgia. Yeah, there are African-Americans living in the Confederation of Canada. It does happen. I got a unique story to...

Jonny Wall

by TheBigEd on Sep 17, 2017
Loving Wives

I work in a small office where we manage commercial real-estate. I have a total of over twenty-two million square feet of warehouse space and over a million square feet of office space. I stay away from retail; the turnover is too great and they require a lot of time and maintenance. I just love Fridays, it's the slowest day of the week. I generally take th...

Stepsister's Surprise

by PantyWarmer on Sep 12, 2017
Transsexuals & Crossdressers

I was twenty when my father re-married. My mother walked out on us when I was six and Dad was always right there for me. Fourteen years raising me all by himself, sacrificing his own personal needs and desires and now that I was grown it was his turn. I believed that and I was happy when he found Jane. β€˜His Jane,’ I would say making a spoof on Tarzan. Jane...

My First Time as a Sissy Ch. 02

by SissyTara on Sep 13, 2017
Transsexuals & Crossdressers

This story is about my journey to being fucked as a sissy for the first time. Part One should be read first. ***** When Raoul left after I had given him the first blowjob I had ever given I was feeling confused. I knew that I had enjoyed it but, didn't know how I felt about having to do it again as he had promised I would have to. I guess I wasn't going to...