Gay Sissy Brother Stories

4,160 results
Orientation
Length
Source
Infinite Scroll

Gang Violence

by JimBob44 on Aug 18, 2017
Gay Male

Chapter 1 David Glasspool knew he was lucky, knew he should feel lucky, but didn't feel very lucky at all. He was tall, six foot three inches, muscular, and very good-looking. His mother worked nights at Ludmeyer Bread so that he could go to Brother Martin High School, rather than one of the public schools in New Orleans. In the tenement building that he a...

My Fantasies Ch. 08

by bjmichaels on Jul 17, 2019
Gay Male

Turnabout is Fair Play I don't know what it is about me that makes people think I am gay. Sure, I'm only 5' 6" and weigh 130 pounds; am shy around girls and display undue reverence towards alpha males and older men - but that doesn't mean I'm gay, does it? Yeah, okay, I admit it -- I am a compulsive masturbator and some of my fantasies involve men's di...

Regina and the Hardcase Pt. 02

by GenghisKen on Sep 1, 2017
Gay Male

"As the bastard leveled the double barrelled shotgun at the thin man, he had the confidence of a schoolyard bully, absent the knowledge that this would be his last act on earth." "Just a handjob mister, that is all you paid for." Eleanor said as she looked up at the haggered man. Eleanor Wiggins was not a new whore. Her demure manner outweighed her misplac...

Sissies love big black cock

by Yelawolf on Nov 16, 2017
Gay

Welcome to the story you crazy sissies and you strong aphla black males. This is from edithis and I want to bring here so you guys can write or read or for the real reason you're here to masturbate. Get your hand, dildos, lube, and whatever else you need to jerk it off. Time to begin the story up. (Thanks for all of the likes and support on this story. I jus...

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You are a Sissy Pt. 03: Body

by Roland15Rollin on Dec 24, 2019
Gay Male

Hello. Hello, sissy. You have come back. You have come back again for another session. Welcome back, faggot. My sexy sissy faggot bitch. I am so glad you have come back. But you have no choice, do you, sissy? You have to come back. You need to come back. You need to hear my voice. It is the voice of truth. The voice that tells you what you are. What you tr...

You are a Sissy Pt. 02: Public

by Roland15Rollin on Dec 24, 2019
Gay Male

Welcome back, sissy. Welcome back, my little sissy bitch. We came so far in our first session. You came so far. You once thought you were a man but now you know better. You are not a man. You have never been a man. You are a sissy bitch. And that makes you so happy. So fulfilled. You love being a sissy bitch. A faggot. A gay little toy for real men to use...

You are a Sissy Pt. 07: Cuckold

by Roland15Rollin on Dec 24, 2019
Gay Male

Hello, princess. Hello again. I see you are back. That pleases me, sissy. It pleases me that you have come back for more of what only I can give you. The truth only I can give you. And we have come so far together, princess. We have come so far exploring the depths of your sissy feminine mind. And your mind is feminine. Make no mistake about it, princess....

You are a Sissy Pt. 06: Slave

by Roland15Rollin on Dec 25, 2019
Gay Male

Hello again, princess. Welcome back. Welcome back yet again to our journey through your mind. Our journey through your feminine girlie mind. We are almost there, princess. We are almost to the end of our journey together. I know that makes you sad but it's okay. It's okay, my sweet sissy. It's okay because we have more to cover and I will always be with you...

"You Go First" 01: Jake Said

by donaldelliott11 on Dec 24, 2019
Gay Male

[Thanks to Ken N. for editing me. This is a story about eighteen-year old college freshmen discovering the pleasure they could give each other when girls weren't around.] *** I didn't lose my virginity until I was in college. In fact, I had very few dates at all in high school because I was so shy. I had no idea why some male and female classmates were so...

You are a Sissy Pt. 04: Women

by Roland15Rollin on Dec 24, 2019
Gay Male

Hello again, sissy. Hello, my sissy bitch. I am so happy that you are back yet again. You love coming back to continue our sessions, sissy. You love coming back because I am helping you. You need my help. You know you need my help, sissy. You need to come out of the closet and let the world know what a gay cocksucker you are. You need to let the world know...