Gay Anal Caption Stories

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Image Inspiration Chapters AI version

by Nissen on Apr 22, 2025

Inspired by the story Image Inspiration Chapters, but this is the AI version. Story is open to public, so anybody can add chapters as they please. But I reserve the rights to delete chapters posted that stray too far from the rules. All chapters must contain anything from a short caption to a full on story based on the image posted at the end of the previous...

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2020 - WIC

by Rekki on May 10, 2020
Miscellaneous

WIC, short for „Weekly Image Captions“, is a project I started this year to post an image caption each week. The characters, scenes and kinks are often different from piece to piece but there are some reoccurring themes like Timestop and Mind-Control, since these are my own favorite kinks. Since March, it‘s possible to choose the character for an upcoming we...

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Kissing Crossdressers Pt. 02

by Candyboi on Sep 13, 2017
Transsexuals & Crossdressers

I awoke the next morning still dressed in Carla's purple panties, stockings and matching bra. The rampant rabbit and the dildo were beside me on the bed. There were traces of the lip-gloss on the duvet and the heady, pungent smell of cum. Carla's panties were stained with the stuff. I figured I had a lot of cleaning and clearing up to do. I felt a sense of...

Kissing Crossdressers Pt. 01

by Candyboi on Sep 13, 2017
Transsexuals & Crossdressers

It started when Carla, my hot sexy wife went away on a spa break a few days with some of her girlfriends. Carla is 40 (I'm 48), has blonde hair, blue eyes, 34DD tits and a curvaceous ass. She works long hours in a busy office as a manager, I work in a local library and my job is far less stressful than hers. And her job has definitely taken its toll on our s...

Them's the Rules

by archibael on Jan 15, 2019
Humor & Satire

(fd, mf, ff) * Betsy is unable to fathom how her roommate is getting everyone to go down on her. There was no way Sophia could be getting this much oral sex legitimately. Betsy didn't begrudge her roommate her pleasures. God knew half of her incredulity was unadulterated jealousy, but the other half... Kmele Colter, for instance. He was a fine, fine spe...

Stephanie's Toy

by cuckoldwishes on Sep 19, 2017
Transsexuals & Crossdressers

I think it's something every man thinks about at least once in his life. What would it be like to wear panties? They are soft, silky... sexy. When I first started wearing panties, was just a couple minutes at a time. I would wear them around, check out how they made my ass look and then I would masturbate and fall asleep. Over time I became accustomed to wea...

A Short One Handed Play

by LeanneSinclair on Sep 1, 2017
Humor & Satire

The scene is a large, comfortable, characterless room in a large, comfortable, characterless hotel, somewhere in continental Europe. The clothes and other items visible in the room suggest a single, male occupant. The shower is running. The television is on, with the sound quite low. On the bed is a magazine, open at its centre pages. The room's tenant emer...

The Rainbow Lounge

by charlessmythe on Aug 18, 2017
First Time

When I was eighteen years old, I heard a rumor that Rainbow Lounge a bar on the other side of Fort Worth was a gay bar. I'd always had 'urges' to have sex with a man but was always scared of trying. My older brother was overseas in the army and I had his driver's license and I looked enough like him for it to pass inspection. So after thinking about it for a...

Fan Fiction Captions

by pornsleuth6 on Apr 29, 2025

I have been making a lot of captions lately, so I thought it made sense to split the captions off from my short story collection (https://chyoa.com/story/Short-Fanfics.46075). They are similar things of course but different enough that I don't want to disappoint people looking for one and finding the other, update to update. The grouping on these will be fai...

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Chris Jones: Pledgemaster Ch. 02

by PhoenixLord on Aug 31, 2017
Group Sex

Author's note: This is a sequel to my first story, My Sexual Adventure, and incorporates many of the characters from the first story, plus a few new ones. This story takes place after the events of Chapter 6, during Chris's remaining college years. All characters are over 18, and all are loosely based on my favorite porn stars listed below. Remember to rate...