Gay Castrated Sissy Stories

78 results
Orientation
Length
Category
Source
Infinite Scroll
SmutMD: The World's Biggest Erotic Literature Search Engine.
© 2026 SmutMD.com
Create your own smut fantasy with AI

Sissy Sundays

by BlinkOneSomething on Apr 13, 2020
Gay Male

It was the summer of nineteen-ninety, I had just graduated high school and was partying like a rock star. Occasionally when my friends would drop me home late at night, I would walk the block or so to a nearby two lane highway that led out of Boston and stick my thumb out, not ready to end the night just yet. I had a massive libido but knew the chances of a...

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....

The Making of a Master

by Littlepoppyhole on Oct 6, 2020
Gay Male

David lay on the dishevelled bed exhausted and still sweating after his recent sexual encounter with a man called Raymond. His hole was leaking semen onto the bed sheets. The sheets also gave off the aroma of anal mucus. This did not perturb David as he was deep in thought about the man he had served. He thought there was room for improvement in his sexual i...

A Pound of Flesh

by SEVERUSMAX on Sep 14, 2017
Gay Male

I was rather annoyed, to say the least, to be interrupted from my sleep that morning, on one of those rare occasions that I attempted to sleep in. Normally, I tended to be too eager to get things done to stay in bed and waste my day with idle semi-slumber. Then again, at this particular moment, I was overdue for some sleep, but I wouldn't get it yet. I was j...

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...

Black Daddy Domination

by AfroerotiK on Sep 14, 2017
Gay Male

Scott Clark hated his whiteness. He wasn't able to articulate it exactly in that way; he claimed to be coming to terms with his submissive nature and his overwhelming desire to serve the Black race. Had he been a bit more self-aware, a bit more introspective, he could have accurately described his self-hatred as stemming from his inherent need to feel superi...

Danny Darling Ch. 04

by bjmichaels on Sep 14, 2017
Gay Male

It's funny how you view things differently in the light of day. Last night it made perfect sense to agree to my landlord Danny's outrageous demands, but now, with the sun shining brightly, and a fresh perspective, I seriously questioned the 'deal' I'd made with him. Yes, he is going to do me a huge favor by driving me back-and-forth to work, so it is fair,...

Mr. One Fifty-Eight Ch. 01

by tazemebro on Sep 14, 2017
Gay Male

Mr. One Fifty-Eight picks up where Chris Donaldson left off. Chris Donaldson and Justin Corvino were roommates during their sophomore year in college, which has just ended. Justin began the year by forcing Chris to suck his cock, and their daily sexual activity gradually grew into an intense, Dom/sub oriented relationship. Chris' feelings for Justin deepened...

They Are A-OK Ch. 46

by fantasyhunter2 on Sep 14, 2017
Gay Male

This is a work of fiction and contains graphic sexual depictions. If this may offend you or you cannot legally view this material in your jurisdiction please exit now. To any new readers who somehow stumbled upon this chapter without having read anything before it: My stories tend to defy categorization. I put this in the gay section because it deals mostl...

Good Red, Evil Red, and The Beast

by Coxswain on Sep 14, 2017
Gay Male

And how a bottom topped me "Mr. Oakley, can you run this message over to my assistant, Mr. Claridge? Could you go right now? I have to arrange for him to take my three o'clock English class; my plane leaves earlier than I thought." "Of course, Professor. Is he in the classroom now?" "No, as a matter of fact, I think he's in the gymnasium sauna." I took th...