Prolapse Gaping Stories

22,937 results
Orientation
Length
Source
Infinite Scroll
SmutMD: The World's Biggest Erotic Literature Search Engine.
© 2024 SmutMD.com

Jay's Sex Club Adventures Ch. 01

by WhiskeyIsGood on Sep 11, 2017
Transsexuals & Crossdressers

Summer 2013, I turned 25 years old. I will not lie and say that I was thrilled or anything like that, to be honest with you, it was quite the opposite. I was not happy in the least bit to be just another year older, as I liked to say. Especially given the fact that at the midway point of my twenties, I still had been unable to find a woman that I could devel...

Coach Daddy Ch. 07

by whatcouldofbeen on Sep 25, 2017
Transsexuals & Crossdressers

It has been several glorious weeks since my gender and in essence , my life, changed. Who was once an awkward bean pole of a young man, was now a confident budding woman. It all started when my boss, Coach Zek, noticed my preoccupation with all the huge men I was now constantly surrounded by. He also noticed that I wore a bra. I'm sure at first he thought I...

The Good Girl Ch. 04

by Katies on Sep 26, 2017
Fetish

If you read, please do the courteous thing, and vote/comment/leave feedback. We authors work hard and it's nice to be recognized. Feedback encourages us to write more. I hope you enjoy! ;)~ ****************************** It had been two weeks since Shannon and I had been to the club for the first time. We'd found out that every month they hosted a "Fantas...

Orc Dominion: Conquest Ch. 01

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

"We shouldn't be doing this," Sarah whispered. "I know," Rosalind murmured back as she brushed through Sarah's long dark hair, "we should stop." "Mmm" Sarah moaned as she pulled Rosalind into a kiss. Her hands wandered over Rosalind's tight body, touching everywhere, exploring everything. Ros responded in kind, eagerly sliding her hands underneath Sarah's...

It's All The Ex's Fault Ch. 14

by acup on Sep 14, 2017
Erotic Couplings

AUTHOR'S NOTE: It's all the Ex's fault It was intentionally written without names. LEGALESE: Don't read this if you are underage, if it is illegal in your area, if it is offensive to you, or if you cannot distinguish fiction from reality. This is a work of fiction. All characters are 18 years of age or older. Copyright (c) 2014 by Acup I woke the next...

Wicked Tales: Little Red's Wolf

by RedHairedandFriendly on Sep 12, 2017
Sci-Fi & Fantasy

Author's Note: This wicked tale is an adult version of Little Red Riding Hood. I do hope you enjoy it. Thanks to deathlynx for willingly reading as I wrote, pointing out a few things I missed, and a great title. If there are more errors . . . it is my fault. ~ Red. ~ ~ ~ ~ Athelyna listened to the tales of old, wondering just like the other boys and girls...

A First Time for Anal Play Ch. 7

by BigMan on Sep 19, 2017
Anal

The rest of the train ride to Charleston was great. We enjoyed the company of Jake and Maria as we ate, got off at stops, talked in the club car, etc. Naturally the best of the ride was the time we spent together alone. Julie proved to be an imaginative as well as totally open lover. We fucked in as many places as we could on that train. We went back in...

Code Name Tequila Ch. 05

by Travel_by_day on Sep 15, 2017
Transsexuals & Crossdressers

CIA agents Chambers, Cho and Juarez were sitting in the meeting room waiting for Black Oak to join them. All of them had received pages early in the morning telling them to immediately come to CIA headquarters. Chambers looked across at Cho and Juarez. As they had for the past week and half, they were dressed as women. Living as women, really, as Black Oak...

Natalie Plays with Mr Herrick Ch. 03

by Voboy on Sep 17, 2017
Mature

As usual on Literotica, these kinds of stories are a lot more fun if you read the chapters in sequence. But of course you don't have to. Enjoy! * * * "Regular tutoring" was, at first, something I insisted we set up at school. Natalie was resistant at first; she'd pouted, her skirted legs indignantly crossed, as we spoke about it before school a couple da...

Willow Palin's Birthday Party Ch. 04

by baranbrat on Sep 13, 2017
Celebrities & Fan Fiction

Morning cam way too early for everyone and most of the guests didn't stir until late morning. The majority of the Palin clan was up when one by one the guests came into the kitchenette looking for coffee. By early afternoon everyone was wide awake enough to begin to feel human again. Todd and Track got the large fishing trawler all decked out and gear stowe...