Gay Sissy Father Stories

4,951 results
Orientation
Length
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Infinite Scroll

Fucking Matron!

by HannahSavannah on Aug 17, 2017
Gay Male

Fucking matron was the national sport at our public school (that’s “private school” for Yanks). It was a rite of passage without which no future Australian captain of industry could hope to attain a Dick Grasso-esque remuneration package. But final year frolics came first. We'd reached 18 and were ready to rock and roll. We were wizards of wanking . . . mas...

Little Sex Toy Ch. 04

by keptsissy on Sep 26, 2017
Gay Male

I'm over a complete stranger's knee, butt way up high with his left hand and huge arm wrapped over my back and up under my stomach. He has the flat inside of his left palm pulling me up slightly off his knee. It hurts. I feel him push up into my stomach. He could pick me up like this, pick me up and hold me upside down if he wanted to, he's that strong. He's...

Swallowing My Friends Cum

by corkscrewjohnny on Aug 18, 2017
Gay Male

Just a little background on me, this may help you to understand my stories better. Then again it may not. I am a white male who grew up in the suburbs, in a nice quiet neighborhood. I went to a private school my whole life, and I guess you could say lived a somewhat sheltered life. My upbringing was a catholic one, which meant everything was a sin or wrong t...

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...

Nephew's Readjustment Pt. 15

by bart_allen on Sep 14, 2017
Gay Male

This story contains femdom, gay conversion, extreme humiliation, BDSM aspects, and frankly, is fairly extreme. If you enjoy it, please check out Power Trip, by wally_west, who inspired this story. ***** Nicholas was able to refrain from masturbating that night and the next morning, but only because of the tenderness of his ass. Without access to his genita...

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,...

His Slave Boy 'Good Wife'

by keptsissy on Sep 19, 2017
Gay Male

I called before I got home. He answered on the first ring. He knows better than to not answer immediately. Before he could say anything I cut him off in mid-sentence. "Naked, at the door in just a pair of sexy heels, nothing else, I want you. I'm hard in my pants thinking of your submissive little ass. Your makeup and hair better be perfect, little boy, fuc...

Little Sex Toy Ch. 03

by keptsissy on Sep 26, 2017
Gay Male

"What have you learned, boy?" He's sitting on my couch. I'm naked and lubricated, can feel the K-Y jelly slippery and wet up between my cheeks. It's just two days since he visited me last. My toenails are glossy pink and I'm wearing the pink heels I got to please him. I'm shaved and moisturized baby soft top to bottom. "That I keep myself ready to play, kee...

Nephew's Readjustment Pt. 13

by bart_allen on Sep 14, 2017
Gay Male

This story contains femdom, gay conversion, extreme humiliation, BDSM aspects, and frankly, is fairly extreme. If you enjoy it, please check out Power Trip, by wally_west, who inspired this story. * The next weekend, Cynthia called her nephew over in the afternoon. It was time to start preparing him for the next phase in her ever growing plans. She knew th...

The Boifriend Ch. 01

by AdmiralSquish on Aug 8, 2018
Gay Male

[pre-story]Content Warning: SUPER gay. Crossdressing. Sissy self-deprecation. There's going to be some unrealistic anatomy later on, huge cock, huge balls, and huge loads. Disclaimer: All characters are 18+[/pre-story] ***** The Boifriend, Chapter 1 "Whelp!" Leo exclaimed as he stood up and gave an exaggerated stretch, feigning a yawn. "Looks like it's t...