Role Reversal Pegging Stories

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The Best Present: Pegging my Man

by silkstockingslover on Sep 25, 2017
Fetish

Summary: A wife discovers her husband is curious about pegging and.... Note 1: This is a Holiday 2016 Contest Story so please vote. Note 2: Thanks to Tex Beethoven, Robert, Dave and goamz86 for editing this story. The Best Present Ever: Pegging my Man I was working from home, stuck with a sick child, when my whole world changed. My work laptop died and...

Prom Night Pegging

by SluttyBisexualGuy on Sep 21, 2020
First Time

*This story contains themes of pegging, female domination, bisexual sex talk, and sexual role reversal. If you're seeking something more vanilla in nature, well, don't say I didn't warn you* Her name was Bridget Ramirez and she was the hottest fucking thing to ever walk the walls of Cheyanne Mountain High School, in Colorado Springs, Colorado. She was an...

'Jenny' & 'Mike': Date Night

by hfernandez1983 on Sep 25, 2017
Transsexuals & Crossdressers

Hi guys, I hope that you enjoy this story that deals with Pegging and Gender Role Reversal. The idea of pegging has always been a hot topic for me. I have tried it in my personal life, though not in the same way as the characters in this story, and have found it to be a highly erotic experience. I have wanted to write this story for a while but have been put...

Pegging Tales: Justin's First Time

by hfernandez1983 on Sep 13, 2017
Illustrated

*-*-* Pegging has been a topic that I have wanted to write about for a very long time. In my personal life, I have yet to do it. It has long been a fantasy that I felt has been left unfulfilled for a while. I have read a lot of stories on the topic and have loved most of what has been published on Literotica. So I thought it was time maybe I write a story o...

Creampies, Pegging & Intimacy

by Here4u2get on Nov 18, 2019
Erotic Couplings

I had to laugh when I heard the music playing and the shower running behind the door of the master bathroom. Dana, my wife, apparently had the same plan as I did about getting ready early that Saturday evening before we met her girlfriend and husband for dinner. Yes, she wanted to see as much of the football game as she could before we had to leave. Though...

Japanese Femdom For Black Men

by Samuelx on Sep 16, 2017
Interracial Love

"Stop making a fuss, Sylvain, and give me that butt," Mirai Kitagawa said, laughing merrily, as she playfully slapped her boyfriend's ass. For ages they'd discussed this. Pegging. The ultimate act of role reversal. The sexual penetration of a man by a woman. An essential part of "Femdom" according to the web. The moment of absolute truth was finally upon the...

When it Finally Goes Right

by sex2us on May 15, 2019
Anal

Most I'm sure would agree that whenever you try something for the first time, sexual or otherwise, it can feel different or even uncomfortable and you are faced with two choices: either give up or continue on learning as you go until it all falls into place. Anna and I decided to give pegging a try, if you don't know what this is look it up or just keep rea...

Sex Adventures with Alisha Ch. 03

by GeorgiaSexAdventurer on Apr 13, 2020
Group Sex

NOTE: This story is the continuation of the Sex Adventures with Alisha series. This story could stand alone, but if you would like to get to know the narrator and Alisha better, then you'll want to read the first two stories of the series. I listed this story under Group Sex because a new character will be added to these stories. The first two stories can be...

Women Enjoying Naked Men Ch. 03

by escriterra on Sep 13, 2017
Fetish

The muscles in her hips she had pressed into use as she fucked fantasy-Darrian the night before were actually sore the next morning as Taryn went through her gym routine. It was a delicious soreness. She looked forward to exercising those muscles so they wouldn't be sore. Taryn was ready. She just couldn't find a guy to peg. So it was good ol' dependab...

Blowback

by dreadknots on Jun 18, 2018
Transsexuals & Crossdressers

Another story! This one is a sorta reversal of a typical mind control scenario, where the slighted nerd ensnares the stuck up bitch. What happens when it backfires and turns a horny guy into a sissy sextoy? Lewd shit, obviously. *** Chloe flicked through the tabs on her laptop's browser, skipping between links and trying to polish up her history paper. Thi...