First Pegging Stories Stories

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All Girl's School: A Cunt Fest

by silkstockingslover on Jul 8, 2019
Illustrated

Editor's note: this story contains scenes of incest or incest content. Summary: A teacher's lez side is awakened by a hot teen. All characters in sexual situations are 18 years of age or older. Note 1: This is a Nude Day 2019 Contest story. Note 2: This story was inspired by this caption photo by @Mistressr3: At the top was the following text: Ever si...

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...

The Making of a Man Ch. 01

by Imakewetspots on Feb 10, 2020
Mature

(Author's Note - First, a special thanks to Literotica author "Cockhole" for his help. I have a mental outline of potential future stories branching off this first piece, each developing characters more fully as the overall storyline progresses. Please feel free to message me, privately or publicly, any constructive criticism, opinions, or ideas to incorpor...

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...

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...

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...

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...

Best Anal Sex Ever Ch. 02

by PrymeUser on Dec 31, 2017
Anal

Well, I thought I was just going to write one story about an amazing anal experience but I really enjoyed the process and we've had a few more fun times since so I thought I'd share them. You could read chapter one to get a little background but it's not essential. This isn't a fictional story. It's a series of actual events which I've tried to recall as acc...

Tease, Party, Peg

by magmacdowel on Sep 11, 2017
Anal

Lynn was examining herself in the standing mirror when her shirtless husband, James, entered the bedroom. His olive-tan skin was still beaded with steam from his shower. She looked back at her dress. It was a teal and coral printed sheath that hugged her curves, even with the back unzipped. "Someone looks nice," James said as he came up behind her and place...

Expanding Horizons

by JacobGoody on Sep 16, 2017
Fetish

Adam was cute from the minute I laid eyes on him at a friends party. Skinny and bearded he was a plaid wearing hipster kid holding his beer and listening to friends tell ridiculous stories about art school. He kept a smile on his face, and whenever there was a pause to drink, his eyes scanned the room, sometimes making contact with mine. Eventually that eve...