Gay Cuckold Training Stories

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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 Metamorphous

by eviltwin52 on Aug 29, 2017
Gay Male

I didn't plan to be a homosexual. I didn't want to be known as a sissy. I didn't want to be used and abused by those who were my friends. I tried to be a normal, heterosexual male. Mother nature had other plans for me. My name is John. I've always been on the small side. My height is 5'6" and my weight was 130. I have a narrow waist, a pert, round bottom...

March Madness Ch. 07

by watchdwag on Sep 14, 2017
Gay Male

It felt really weird waking up beside another man in my bed. My ass was pressed against Larry's cock as I woke with his arm gently draped across my waist. It was a position to which I was accustomed with my girlfriend Sandy as she would often cuddle close to me in a spoon position in the bed. I looked over and Larry appeared to be dead to the world as I pull...

Sissy Cuckold & The Old Bull Ch. 02

by DirtyDaddyHunter on Sep 19, 2017
Gay Male

"Now for your turn" leers the old bull, stroking the mushroomed head of his gnarled old cock. The old man starts to get hard again and grabs the husband's head. He slams his cock back in the husband's mouth, brutally facefucking him. "Is that what you want Sissy? To be Daddies pantied cocksucker? "The husband chokes and gags on this vile old man's big cock,...

Tom and the Neighbors Ch. 02

by Leftahead on Sep 19, 2017
Gay Male

This is a continuation of Tom's story. Reading the first installment will fill you in on many of the pertinent details, but it's not a life-changer or anything; Tom hangs out with his neighbors and they get it on. He touches his first penis, but doesn't go any farther. Please do enjoy part 2! * Tom thought a lot about that evening over the next few days....

Just Not Enough: A Gay Cuckold Tale

by CinaedeFuri on Jun 8, 2020
Gay Male

"Ooh, yeah, fuck me, baby!" Dawson screamed, as his husband was fucking his hole. But for Christian, it was just another rote fuck with his husband. He loved that Dawson was a verbal bottom who loved getting his hole plowed, but Christian wanted to top sometimes too, and Dawson didn't like foreplay either. He wanted to get right into the fucking. Still, Chri...

My Life as a Cuckold

by HerLittlePiggy on Sep 14, 2017
Gay Male

I heard the door open and my wife stumbled in. It was late but no later than her usual night out with the girls. She staggered into the bedroom and I could see in her eyes that she was drunk, which was also the norm for her weekly girls night out. I knew what would come next. She peeled her clothes off and left them in a pile beside the bed which creaked...

My Role in Porn

by Cyanlot on Aug 18, 2017
Gay Male

Like any twenty-two year-old guy whose girlfriend had just dumped him, I was at a bar, drowning my sorrows. I didn't know the bar. Not wanting to run into any acquaintances, I'd picked a dive a few miles from my neighborhood. I'm not much for hard liquor, so I was slugging down beers and spending almost as much time going back and forth to the john as drinki...

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...

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...