Gay Sissy Bride Stories

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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...

Sissy

by MVP6 on Jul 15, 2020
Gay Male

This is my fifth letter describing my expanding awareness from a naive man with a desire to suck a cock to a man willing to explore his seedier side. (M+/M, oral, anal) In my first letter "Costume in a Costume" I describe how I dressed as a girl in a Halloween costume to trick an unsuspecting man into letting me give him my first blow job. In my second...

Bride of my Father-In-Law Pt. 02

by RSchwuler on Jun 8, 2020
Gay Male

Standard warning: this is a very over the top, far-fetched work of fantasy. It contains lots of humiliation and some taboo sexual contact between a man and his father-in-law. Please skip if it's not your thing. Otherwise, enjoy. ***** Roy spooned me, pressing his hairy chest and belly into my back. We were both still slick with sweat. His boner was growing...

Bride of my Father-In-Law Pt. 04

by RSchwuler on Aug 24, 2020
Gay Male

You know the drill: over the top, far-fetched smutty work of fantasy. It contains lots of humiliation and taboo sex between a man and his father-in-law, as well as some non-consensual involvement of the protagonist's actual father and some stuff involving food. Skip it if it's not your thing. Otherwise, enjoy. On feedback: I get a lot of anonymous messages...

Outed and Married

by keptsissy on Sep 26, 2017
Gay Male

He always threatened me with being exposed to my coworkers, to the world as the sissy I am to him. Usually it was part of what I thought was his dirty talk, sex talk. He'd tease me with it. He'd be deep inside of me, slow fucking me, talking dirty into my ear. Or he'd have me restrained and be masturbating me as part of 'my reward', as he called it, and woul...

Andre Finds Love Pt. 02

by eviltwin52 on Aug 18, 2017
Gay Male

In chapter 1 I told how I first became aware of the power and allure of black cock and how I met my wife Lee. My new bride Lee, and her lover, Leshaun were still on our honeymoon and were due back in 2 days. I'd been invited to my in-laws while Lee was off on her jaunt. Dad, my father-in-law, and I just watched his wife get blacked fucked. Dutifully, we...

It Could Be Worse Ch. 04

by eviltwin52 on Sep 14, 2017
Gay Male

In part 3 I was surprised when my wife Cin brought Bonnie home to witness me welcome Stan. Bonnie filmed the ritual on her cell phone, me on my knees kissing his cock and balls through his trousers, thanking him for driving the 4 miles to fuck my wife. Stan indeed fucked Cin that night. It was quite an orgy. Bonnie rode Stan's face while Cin rode his manly...

It Could Be Worse Ch. 03

by eviltwin52 on Sep 14, 2017
Gay Male

Recap: Cin has "softened" my looks so that I appear less masculine to her lover Stan. It continues below. Married! I asked and she said yes. Cindy and I were wed in a quiet ceremony in a courthouse by a Justice of the Peace. Our only witness, a clerk in the building at the time. Our honey moon did not include her lover Stan. For that I am thankful. But...

Jo and Mike

by skinnysailor on Nov 12, 2019
Gay Male

I've got the perfect job. I'm an interior designer at C###### the nationwide premier designer builder of exclusive homes. I mean, if your dream home will cost less than two million, don't even bother calling. Right? I mean, where else could a five foot tall, third generation Vietnamese Canadian, be allowed, even encourage to wear eye liner and nail polish t...

Owned:Fantasy Becomes Reality

by silkstockingslover on Sep 14, 2017
Gay Male

Note 1: This story was written and is dedicated to a true wannabe faggot-cuckold Dave. Note 2: A special thanks goes to Estragon for his copy editing work. 1. THE BEGINNING I blame Literotica. No seriously...if it wasn't for Literotica, none of this would have happened. Now in all fairness, some would argue it is my fault; as it was my own stupidity a...