Debby Ryan Stories

4,400 results
Orientation
Length
Source
Infinite Scroll

Life on the Ranch Ch. 03

by phoenixcinders on Jan 28, 2019
Transgender & Crossdressers

I've received many comments stating that they prefer shorter chapters to longer ones, so I've decided to try shorter chapters. As always, all characters are of the age of 18 or higher. ***** Bzzzz! Bzzzz! Bzzzzzz! Bzzzz! Bzzzzz! Bzzzzzz! Uhhhhh, I'm so exhausted. I can barely find the strength to shut my alarm off. 4 AM came quickly, my body aches from a...

Debbie's Awakening Ch. 04

by jlenil on Sep 15, 2017
BDSM

I strongly suggest reading the first 3 chapters before proceeding to this one. ***** Gus was clearly very frightened, but also, quite obviously, extremely aroused. Debby went over to his side and showed him the documents that he would be signing. "I will remove your gag, Gus, but if you make any disturbance, there will be a price to pay." She then ungag...

Boring Betty

by Softly on Jul 14, 2020
Mature

Hi, I'm Betty Reed, widow of Dr. Fred Reed, MD. At age fifty-eight, I am just your average widow. I stand five feet, two inches, and weight one hundred and thirty-nine pounds. There was a time that I was considered very pretty, with a damn fine figure. Gravity has done its work, so now, some would say, that my breasts have "gone south." I spend my time chat...

American Beauty

by FrancisMacomber on Sep 18, 2017
Loving Wives

When I pulled open the door to the tavern, the sound that came pouring out was like a crowd at a sporting event. "And I bet I know the name of the game that's being played," I thought wryly. As I walked in, the noise level dropped noticeably, but I ignored the attention I'd drawn and scanned the room until I spotted Marge waving at me from the table she'd c...

My Little Penis and Me Ch. 02

by mceh501 on Sep 12, 2017
Fetish

(((Note: All Characters in the following story are based on real people in my life, however it is not a true story. All the character's names are changed. All of the following characters are over 18. This story is about humiliation and a person with a Napoleon Complex, so to speak. If sph isn't your thing, move on.))) Hi, it's Tim again, I'm still living...

Desperate Debby

by justin grimbol on Sep 1, 2017
Group Sex

I sat on a beach chair stroking my dick. It was nice. My dick liked the fresh air. I liked masturbating outside. The possibility of being caught reminded me of having sex at boarding school. In order to have sex at boarding school you would have to go into the woods or sneak into a classroom at night. Getting caught was easy. One time the entire track team d...

High School Reunion Payback

by Slirpuff on Sep 12, 2017
Erotic Couplings

I'd like to thank my editor Wolf Vixen for her help on this story. I wrote this for all the non-jocks, the people who were never good enough to be in the "In" crowd and all the students who studied there asses off, made it and could finally get the last laugh years later. As they say, "This one is for you." I read the announcement and as I did, I reme...

What This Country Needs

by Joe Average on Sep 1, 2017
Humor & Satire

"Just as she was about to leave, Monica Lewinsky told President Clinton that there was 'something serious' she needed to talk to him about, something she had learned from a friend. A reporter for Newsweek, Michael Isikoff, was working on a story alleging that the president had sexually harassed a woman named Kathleen Willey outside the Oval Office in 1993 .....

Debbie's Awakening Ch. 03

by jlenil on Sep 15, 2017
Fetish

It's now been several years since Debby and I entered our new arrangement and it has worked out very well for us. Deb is in charge and I am still delighted to be her slave. Having a cigar-smoking, dominant woman for a wife was not something I ever would have dreamt that I wanted, but sometimes life takes us down paths that we never would have expected. We...

Saturday Morning

by jjcole on Sep 16, 2017
Romance

Saturday We had known each other since middle school and had dated off and on since. When I wanted to celebrate anything or she needed to celebrate anything the other was there. We lost our virginities to each other at the prom even though we were technically with others at the time. Of course we lost those others when they learned who our prom dates were....