Gay Submissive Sissy Stories

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Submissive Sissy for 'Her' Man

by keptsissy on Sep 28, 2020
Gay Male

He toys with the lace ruffles on my panties. His fingers move over the ruffles and up and down the crack of my butt. I flick my tongue over the hole of his erection and then take it deeply into my mouth, holding it at the base straight up. His eyes are closed as he lays naked on the bed, his huge hard cock sticking up off of him. I start to pump, start to ma...

First Time Sissy Sub

by stevn on Aug 31, 2017
Gay Male

My first time was in a booth at an adult video store with an older guy. This is a work of fiction, but if it came true... Please email any comments to the contact on my profile, I would love to hear from you. I'll follow this up with part II. ***** I had placed an ad on Craigslist while on vacation alone in another town. It said: "Submissive sissy bottom...

PIXIE Sissy Stripper Ch. 03

by EROTICbearscribe on Jan 6, 2020
Gay Male

Darryl Powers was on his way to one of the two popular nightclubs he owned. His new sissyboi, Benji, was beside him. The boi looked pensive and vulnerable, especially sitting next to Darryl. At 6'5 and a muscled but well-sculpted 230 pounds Darryl dwarfed the, for lack of a better word, 'petite' college boy sitting next to him. Anyone seeing the two pass b...

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...

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....

Obsessed with BBC

by Subkoksukr4u on Jun 26, 2019
Gay Male

I'm not sure what started this obsession of mine. Somewhere over the past 10 years or so something changed me. I day dream of submitting to black cock almost constantly. If I'm lucky I have real dreams about sucking BBC. The first time I had the privilege of sucking black cock was when I lived in Hawaii. Up to then I had sucked plenty of cock but would trad...

High and Low Ch. 05

by bisexualsmoker on Sep 16, 2017
Gay Male

Simon and Brenda's sex life definitely picked up a step. She began using strap on dildos on him. Fucking his ass raw while he squealed in delight. "So you want to be a fag boy! " she would admonish him, as he grovelled on all fours. Brenda battering him from behind with a fury so very unrepentant. He would swivel and moan in glorious delight. The double ac...

Little Sex Toy Ch. 05

by keptsissy on Sep 26, 2017
Gay Male

I'm squatting in the middle of his cold cement basement floor, just over the drain in his laundry room, sitting back on my high heels. The 4" spike heels he insists I wear now around the house, wobble in them and get whipped for it, walking or squatting. He says a 'lady-like' little bitch should know how to wear high heel shoes. Leather, padded restraints...

Suck Thy Neighbor Pt. 02

by ret123 on Sep 23, 2019
Gay Male

I was at my lake house wondering if I was going to have sex that weekend. Although I was a masculine guy who appeared to the world (including my wife) to be a normal married man, I had discovered that I liked to be subservient to men sexually and I had managed to hook up with my neighbor at the lake. I learned that my neighbor liked to have his dick sucked b...

I Turned Myself Out Ch. 03

by drmweaver705 on Aug 24, 2020
Gay Male

"Warning: this video is designed to turn straight men into gay bottoms. Don't say you haven't been warned..." The female narrator had a breathy, clear, commanding voice. It was a voice to be obeyed. "You've stripped yourself naked and stretched your ass in preparation for the arrival of your first ever top..." In fact, I was naked, lying in the marital b...