Literotica Unexpected Proposal Stories

351,580 results
Orientation
Length
Source
Infinite Scroll
SmutMD: The World's Biggest Erotic Literature Search Engine.
© 2025 SmutMD.com

Karen's Secret

by goddamusername on Dec 19, 2017
Romance

Please click on the "Start Game" button on the sidebar while reading this story. Every choice in the story will count towards the way the relationship between you and Karen is affected. Some choices will also determine whether or not certain content will be available/visible in the story. Not initializing the game might lead to some inconsistencies...

Open in Reader

Workplace Agreement

by Alternate Path on Apr 29, 2025

The morning sun burst through the office windows, painting the walls with a warm glow that matched the vibrant energy buzzing through the space. Mark stepped through the door, greeted by the lively hum of chatter and the clatter of keyboards. The air was infused with the scent of freshly brewed coffee from the break room, mingling with the subtle hint of exc...

Open in Reader

Unexpected Proposition

by readcarefully on Sep 14, 2017
Erotic Couplings

I didn't expect to be propositioned as soon as I sat down at the hotel bar with the DJ traveling from Shalamar to Biggie. This Amazonian princess was 6 feet tall, natural curls to the ceiling, titanium glasses, hips to keep her Celine maxi dress from touching her Jimmy Choo heels and sculpted arms that limply dangled her Balenciaga wristlet. She was whispe...

Business AND Pleasure

by justachicky on Sep 14, 2017
Erotic Couplings

I checked my make-up and hair briefly in my vanity mirror before stepping out of my truck and adjusted my skirt and jacket as I walked toward the front door of my next appointment. It had been a long day, and my mega-watt smile was starting to dim a little. I opened the door, and looking around, took in the very nicely furnished offices and the diligent re...

Dildo on a Pole Pt. 02

by UniqueWWETales on Dec 11, 2018
Celebrities & Fan Fiction

Smackdown Women's Champion Becky Lynch found herself in her locker room a few days removed from her first ever encounter with Natalya in a match so brutal, so humiliating, Dildo on a Pole. That particular match made her a better Champion and truly proved Natalya wrong. She wasn't a weak Champion, but a proud and strong one. She beat Nattie in her own game, w...

Big Woman's Guide To Anal Sex

by Samuelx on Sep 13, 2017
Anal

This here is the story of Belle. A plain-faced, thick-bodied, wide-hipped, big-bottomed, blonde-haired, green-eyed, alabaster-skinned plumper from a small Iowa town. Belle had never been what anyone considered pretty. All her life, she'd been the fat chick who never gets to have any fun. The chubby loner. The lonely plumper. And many other fun euphemisms. On...

Break the Gilded Cage Ch. 02

by Elenia26 on Sep 16, 2017
Novels and Novellas

Two weeks later, Julian entered the hot city of Merrakath by boat. In his possession were visitors' passes to the palace. He was met at the docks by a delegation of the palace, which escorted him into a carriage. As he rode through the city, he watched out of the windows. The people seemed fairly happy and content for such a cruel-seeming lord. He kept the...

Lazy Sunday Afternoon

by Cromagnonman on Sep 13, 2017
Romance

I was inside her, I couldn't have gotten any further inside her without stuffing my balls in as well. Her clit was jammed between our pelvic bones and my balls were resting against the puckered lips of her ass. I could feel her down the full length of my shaft and it felt so good that I was having to think about my ex to stop myself from cumming. "Oh my God...

How to Score Your Sex!

by Soul Janitor on Sep 1, 2017
Humor & Satire

Perverts who have found themselves in a bit of a rut ever since Hustler ceased publication of its annual Hot Mennonite Chicks issue got an unexpected bonus this week when the Department of Health and Horny Services released the long-awaited rules and regulations for formally scoring a session of sexual intercourse. The complete rules are available online for...

Enslaving Chloe

by visviva2 on Sep 14, 2017
BDSM

Edited by Rosmarina (whose advice and assistance are much appreciated) Please do not reproduce this story without permission. == Prologue == This story is a work of fiction, but it is based on true events. It is fiction in the sense that what I have described here represents a distilled version of what actually happened. I have tried to remain true to the...