Gay Prostate Stories

30,137 results
Orientation
Length
Source
Infinite Scroll

The Tide Has Turned

by Sczar on Aug 30, 2017
Fetish

In 2037, a NEW WORLD ORDER was positioned firmly in place. Decades before, many of us thought by this time there would be wars to fight over natural resources or we'd be on the receiving end of a constant pummeling by natural disasters owed to climate change. Others thought perhaps we would face an evil world military superpower threatening to destroy all th...

Sissy Chantel, New Reality Ch. 06

by Sissy_Chantel on Sep 15, 2017
Transsexuals & Crossdressers

Chapter Six: On My Way to My New Life at The Agency. Well the day has come for my transition in my life to becoming another sissy maid and sissy slut (aka: comfort girl) to 'The Agency'. Over the last two hard and humiliating weeks Master Camron and Sir Gage now as paid agents to my joining the team at 'The Agency' have helped me sell, give away or toss o...

Alexa and the Virgin

by kisslessvirgin on Sep 17, 2017
First Time

At twenty years of age, I was still a virgin. I'd never even kissed a girl. I certainly wanted to, but my lack of confidence prevented me from making any moves. Depression and mild social anxiety plagued me all my life, and I feared rejection. My horrible self-image sapped any chance in my mind of even a moderately attractive girl falling in love with me....

The Journalists Ch. 02

by Wifetheif on Sep 13, 2017
BDSM

The next morning I awoke with the alarm and awaited my Goddess's orders. My hard on in its cage felt wonderful. Goddess Erica requested a through massage and demanded the proper praise. I extolled her virtues as I massaged her magnificent body head to toe. Though a new experience for me it seemed as natural and familiar as breathing. A short time later God...

Bless Me Father for I Have Sinned

by AfroerotiK on Sep 14, 2017
Erotic Couplings

I'm a pervert, and an unapologetic one at that. I'm so completely confident and comfortable with my sexuality that I refuse to compartmentalize it, lie about it, or be ashamed of it. I'm free from society's pressure to conform and that is a joy most people will never experience. To most people in a sexually-repressed society, being unashamed of your sexualit...

Dreamin for Semen

by Formerly Ty on Aug 18, 2017
Fetish

Hello, my name is Stacy Keibler, and I'm 24 years old. I am about 6 foot 1 inches tall, and weigh somewhere around 125 pounds, depending on when you catch me. My measurements are 34B, 24, 35. I have dark black hair, and I guess you could say I'm pretty good looking, as I've never had any trouble attracting men. My eyes are brown, and my best feature is proba...

Finding Each Other

by silvarman on Sep 16, 2017
Group Sex

I have had many interesting relationships over the years but none that compares with those of last year. In February, I met a woman who was an investor in a business scheme that I was investigating as a radio talk-show host. She was attractive and looked to be an easy mark for a con artist. I spoke with her and within a few days she had canceled out on her b...

Shemale Assassin

by joshy029 on Sep 12, 2017
Transsexuals & Crossdressers

Author's Note: This story was written a long time ago, and only recently have I thought about posting it. As with Opposites Attract, this story was inspired by a roleplay. It's set in post-revolutionary America, in the Assassin's Creed universe. A huge thank you to my good friend Kayla for roleplaying this with me and inspiring this story. All characters...

Such A Small World

by oldhippie1949 on Sep 13, 2017
Group Sex

Normally, I write a warning about the contents of this story. I write about the age limitation to read this story. This time I'm not writing any warnings. This story is about fun, satisfying sex and if you're too young to appreciate it, go somewhere else. ------------------------------------- Inspired by Jeziebell82 I watch her several times a week. Her b...

Sweet Escape Ch. 03

by sailinggoddess on Sep 16, 2017
Group Sex

Sweet Escape – Ch 3, Sweet Release in the BVI's On this, our first passage on the new boat - Sweet Escape, I find that my hand-picked crew is working out just fine. And not just for me, it seems that everyone is getting along. In fact, I think that everyone has really bonded. None of that "first passage crazies," with half the crew sick and the rest on yo...