Gay Sissy Brother Stories

4,160 results
Orientation
Length
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Infinite Scroll

How I Became a Sissy Slut

by DixeenormousToo on Sep 15, 2017
Gay Male

I wish I knew I had these sissy urges when I was younger. Who knows, instead of getting married, having kids, and living the "American Dream," I might have discovered hormones, worked my body into shape, and become a tranny porn star. After all, how often does the American Dream really work out anyway? I'm unhappily divorced, my oldest is on his 6th year of...

I Hope He Didn't See Me Ch. 02

by Kent100 on Aug 17, 2017
Gay Male

As I stared at the floor, still flustered and too embarrassed to look my brother in the eyes, he stepped away from me and walked to the other side of the kitchen. "Hey man, I came over to borrow that door hole drill set you have. I'm going to hang the doors at my new house today and it would sure come in handy," he finally spoke. As he made no mention of k...

Sissy Dream Come True

by Sjen451 on Oct 6, 2020
Gay Male

It was Friday and I had one job left before I could start my weekend. I didn't have much planned other than watching some of my favorite sissy porn and playing with a few of my larger dildos. Not too exciting, but it's how I spend most of my weekends when I don't have other plans. Today I wore my red lace panties under a pair of black break-away running pa...

What Being a Sissy Wife Means to Me

by SissyWife on Aug 18, 2017
Gay Male

I am a sissy wife. I hate clichés as much as the next girl, but sometimes they make for the most apt of descriptions. I have a job, friends, and a life. I go out, I go out for movies and drinks. I enjoy long walks and drives, and I love travelling to new places and locations. And yet, there was something missing. There was something that was needed. I found...

Chubby Sissy Meets His Daddy

by vulpinechub on Sep 19, 2017
Gay Male

The following story is a work of gay fiction. It contains sexual acts between males. This story focuses on: Humiliation, diapers, sissy play, domination. Copyright 2014 -- Feedback is appreciated. * My university decided to cancel classes for the day, but it was too late: I was stuck in the worst traffic of the decade. Mainly due to the incompetence of b...

Sissy Veronica

by slavegurl_veronica on Sep 16, 2017
Gay Male

Hi. My name is Veronica. I am a 21 year old, 135 pound, pale white sissy boy with dark brown eyes and hair. My master is Derek. He is 6 ft 5 in, 175 pounds of beautiful black stud. I have a sissy playmate named Alex who is also Derek's pet. As I already described in an earlier story, Alex's sister Cecilia is responsible for hooking us up with Derek and intro...

Uncle Saul

by Kent100 on Jan 13, 2018
Gay Male

I would like to do two more installments to this if there is any interest... one about Danny... one more about Uncle Saul's business... all comments are welcome and will not be deleted... When I was a young kid, both of my parents were tragically killed overseas. They were on vacation in Israel and were collateral casualties in a café bombing. They were ne...

The New Gym Member

by exaucer on Sep 14, 2017
Gay Male

Wanting to get in to better shape I decided to join a nearby gym. Moreover I was feeling the need to look at other men naked. With your experience you will know the type of young man I am. I am the one who spends longer than is necessary in the shower, stealing looks at other men's cocks. I am the young man who is slow to get changed, sitting there pretendin...

Beach Trips: The Final Chapter

by Universal_Thirst on Aug 22, 2017
Gay Male

The final chapter of Beach Trips, after Beach Trips & Road Head, Beach Trips & Sex On The Beach and Beach Trips & True Romance. A burst of sunlight coupled with the sound of blinds being opened woke me suddenly. I sat up, aware of the smell of coffee and the sensation of nakedness. Chad sat on the edge of the bed, wearing a tank top, shorts and a huge grin....

Party Pizzazz Ch. 02

by bjmichaels on Oct 6, 2020
Gay Male

Party Pizzazz Ch. 02 by BJ Michaels If Tommy hadn't kept such a close eye on me all night at the party I would've ended up as a boy-toy for one of those rich men. That's what he told me afterwards in the car on the drive to his apartment. "Lucky for you I happened to overhear those five assholes bidding on you or you'd belong to one of them now," he said...