Gay Sissy Brother Stories

4,160 results
Orientation
Length
Source
Infinite Scroll

"You Go First," Samantha Said

by donaldelliott11 on Jan 21, 2020
Gay Male

[Most authors love feedback. Please let me know how I did.] This is the third story in this series. You will want to have read the other two. https://www.literotica.com/s/you-go-first-01-jake-said https://www.literotica.com/s/you-go-first-02-john-said + + + + + + + + Jake phoned me Tuesday morning and told me to come visit him that afternoon. His paren...

How Did This Happen to Me?

by bjmichaels on Dec 12, 2018
Gay Male

I live in a very expensive condo in one of the most exclusive and prestigious buildings in town. Most of my neighbors are very wealthy retirees. They generally purchase their condo's with cash. I have a five-year plan where my condo will not only be paid off in full, but I will also have a net worth in seven-figures -- yes, you heard me right -- I am thirty...

Bikini Boi

by MySissyWorldx on Oct 3, 2018
Gay Male

My Brothers Troublesome friends... Note: everyone is of a legal age, and names have been changed for the sake of this story Enjoy *** My first time was more than a little bit terrifying, but enriching to my life beyond my wildest dreams. It began on a family holiday, just after my older brothers 21st birthday, him being 2 years older than I was at 19. Be...

Uncle Marty

by Marty Fisher on Dec 23, 2019
Gay Male

Editor's note: this story contains scenes of incest or incest content. ***** This is a spinoff of my Brotherly Love series where my brother's son discovers his uncle's special talents... It was a hot summer day late in the month of August and I was cleaning my lawnmower in the coolness of the garage when my phone rang. I looked over at it and saw that it...

Andre Finds Love Pt. 03

by eviltwin52 on Aug 18, 2017
Gay Male

See chapter 2 where my father-in-law fucks me while my wife is away on our honeymoon with her black lover. For those of you who wanted to know what happened to joanie in the final chapter of "It Could Be Worse", the mystery is solved. ***** Part 3: Tomorrow, I thought to myself happily. Lee Anne will be back tomorrow. And her black lover, Leshaun. I...

"You Go First" (Ch. 10)

by donaldelliott11 on Mar 2, 2020
Gay Male

This is the 10th in a series. "Samantha" was the 3rd chapter and "Donnie" was the 4th. I regret that my inconsistent use of titles prevents Lit from properly displaying the series. [Writers love feedback. Please comment on and rate this story. About 99 readers out of 100 do *NOT* bother to do either. Comments help authors improve their writing; star rating...

Little Sex Toy Ch. 07

by keptsissy on Sep 26, 2017
Gay Male

The cum all over my face mixes with the tear smeared eye makeup. It's running down my cheeks. It's in my hair, on my neck, I'm covered with cum. The first man that came in my face came huge. He choked me too, deep throat fucked me and made me cry. I've been crying and tearing up ever since. That was three hours ago. He had very large spurts that soaked me,...

Cream Puff Ch. 02

by RubixStu on Mar 12, 2019
Gay Male

When I woke Sunday morning, I was completely nude. I'd showered and removed my makeup before bed. The image in the mirror as I pissed standing up was totally male. I was clearly a man, in appearance at least. Sure, I was totally hairless, but that didn't make me less male. Inside I didn't feel manly. I didn't feel independent, willful, or strong. I felt vu...

Special Inducements

by bjmichaels on May 1, 2018
Gay Male

I was reluctant, but my ex-boyfriend Brian talked me into going to his younger brothers graduation pool party. We were sitting in my car in the parking lot of the liquor store. He had bought two kegs of beer and I helped load them in the car. "Why should I torture myself staring at all those eighteen year-old hard bodies?" I jokingly asked him. "Because yo...

Fixing the straights

by cdbaby on Dec 28, 2016
Gay

You wake up and prepare for your day, unaware that this would be the last day you would be considered straight. You shower as you did every morning and felt the water's warm touch as it cascaded over your skin. You could stay here forever if you could. But you need to start your day and the hot water would run out before long. You wash your hair, then the re...

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