Pegging Surprise Stories

136,140 results
Orientation
Length
Source
Infinite Scroll

Biracial Somali Dominatrix

by Samuelx on Sep 17, 2017
BDSM

Muslim women are supposed to be boring, dull and repressed, that's what a lot of otherwise intelligent people believe. My name is Mariam Jabari and I'm here to refute these absolutely false claims. I was born in the City of Ottawa, Ontario, to a Somali immigrant father, Ahmed Jabari, and a white Canadian mother, Marilyn Samson. I am the daughter of two very...

Discovering Mistress Sarah's World Pt. 04

by oneguy4fun on Sep 12, 2017
Transsexuals & Crossdressers

Special thanks to Mistress Sarah and Miss May and Miss Mill who are my motivation for this story. Thank you for your guidance and wisdom and for the privilege of serving you and writing about you. Chapter 11 Discovering the Girl in Him For the first time since he arrived at Mistress Sarah's house, Josie was left alone in silence. His cock was still thro...

A Latex Crossdresser's Dream Pt. 02

by shinyglove on Aug 20, 2019
Fetish

Please read A Crossdressers Dream part 1 before moving on to this story. *** I was glued to the big screen as my wife helped the 11 inches of strippers cock ease into Karen's well lubed ass. Karen was enjoying every inch. "That's it big boy fuck that sweet latex ass, fuck it hard, fuck it deep," yelped Karen. My wife was also very vocal with encouragemen...

White Girls Better For Black Men?

by Samuelx on Sep 16, 2017
Interracial Love

Shoot. This stuff feels really good. I smiled to myself as my girlfriend Judy Anne Henriksen worked her strap-on dildo deep into my asshole. I stroked my nine-inch Black cock as my sexy, blonde-haired girlfriend fucked me in the ass. Judy smiled fiercely as she slammed her dildo deeper inside of me. Hot damn. Now this is some seriously kinky stuff. And you k...

Would You?

by Dragonologist on Mar 13, 2018
Toys & Masturbation

Would you? This question is being asked because, a week ago, we received a message on Facebook saying we should check our email for instructions because our lives were about to change. Normally, I simply dismiss random messages, like this, from an online person who I don't know, but the name that showed up was Mistress Trudy. It's the same name my wife use...

Sunny Days and Watering

by Kevsta on Sep 16, 2017
Fetish

There was a light breeze in the air, as he hung the washing on the line. It was so sunny, it had seemed a waste to not do the towels, and as he had time, he had stuck them in the washer. As was usual though, he was naked. The garden was quite private, only really overlooked where he was now by the back window of next door, but they were at work, so he was sa...

Kiss of the Spider Woman Pt. 05

by voluptuary_manque on Sep 25, 2017
Sci-Fi & Fantasy

"Jared!" Jared Andrews froze in mid-rant just as he was about to take the keyboard from his computer and throw it through the offending monitor. For the umpteenth time he had checked his work, for the umpteenth time he had sent 'execute' and for the umpteenth time it hadn't worked. He turned around to see Melissa Koenig, matriarch of The Farm commune, stand...

FemCon 2048 Ch. 01: The Pegging Seminar

by shankinauthor on Dec 24, 2019
Fetish

Note: All characters featured in this story are over 21 years of age or older. Note 2: Thank you to blackstallion21 for helping me edit. FemCon 2048: The Pegging Seminar ~Background~ Every 3 years in mid fall, a female domination convention is held in a major city in the United States. A few decades back most cities would feature protests against this k...

Twenty-One More Questions

by silkstockingslover on Jan 1, 2019
Reviews & Essays

Summary: Jasmine responds to the most frequent questions asked by readers. Thanks to: Tex Beethoven, Wayne, and Robert for editing this essay. This isn't really a sequel, although it's a second part, as it addresses questions I didn't answer in 2017's Twenty Questions. 21 More Questions After 2017's 20 Questions, I received many more questions. I have n...

The Shameless Slut Fails Her Exam

by erinyahn on Sep 12, 2017
Group Sex

This is the second story in the "Shameless Slut" series. Each of the stories is standalone, but you may appreciate this one better if you read the other one as well. The nature of these stories is that the protagonist is trying new things as she discovers her sexuality, so each story will touch on different kinks and genres. So, some stories might be your th...