Waking Up Stories

354,405 results
Orientation
Length
Source
Infinite Scroll

Spinal Meningitis is No Joke Ch. 01

by LexxRuthless on May 29, 2018
Erotic Couplings

This is a big dick story. If you don't like big dick stories, you probably won't like this. ***** My name is Joshua, but everyone calls me Josh except my Mom. When I was 16, I contracted bacterial meningitis and almost died. Before that, I was a typical high school nerd. I was 5 foot 2, just over a hundred pounds, and I was an avid reader of sci-fi, fantas...

Sammi Goes to College

by Sissy_Sammi_ on Dec 10, 2017
Transsexuals & Crossdressers

4th part to Sammi's story. After Sam graduated from high school, and knowing he'd be moving to college by the end of the summer meant he was just killing time until then. He worked for most of the summer at a restaurant as a server, and at night Sammi worked as a cam whore. He made some extremely good money by the end of the summer, and he was extremely pro...

The Motorcycle Chronicles Ch. 01

by TripleJJJ on Sep 16, 2017
NonHuman

Chapter 1: A new life The engine in my brand new, black, Harley Davidson Dyna Super Glide roared into life as I prepared to start out on my new life. A new life that would lead me far from the small town that I'd lived since childhood, and away from everything I'd ever known. A brand new world was waiting for me and I was ready to greet it full on. Sure I w...

Tight Fitting Jeans

by theoldone on Sep 13, 2017
Erotic Couplings

I was setting at the bar of my favorite hangout just drinking a beer and looking at the mirror behind the bar. I just happened to look it the door in the mirror when the most beautiful girl I had every seen come though the door. She seemed a little nervous and looked all around the place. I could tell she wasn't looking for any one particularly but just lo...

All Said In A Look

by Brockleigh on Sep 14, 2017
Erotic Couplings

"So what time will you be back?" I called out. I smiled as I watched my wife move around the front of the house in her last second preparations before going out. Her lovely figure captured in an elegant silk blouse and knee length skirt, with a pair of pumps accentuating her toned calves. I watched her toss her long, thick, auburn hair as she put on the last...

Joan Gets a Surprise Ch. 04

by JustALittleCrazy on Sep 14, 2017
Novels and Novellas

October 19th - Tuesday: We sleep late and wake just short of 11am. I'm still tired. We shower and then go to brunch. When we are finished, Joan wants to hit the beach. Both John and I tell her we are too tired and we are going to relax in the room for quite awhile. Joan strips and grabs a towel and heads for the beach again. God, she's dark as hell already...

Slave Silk's Diary: Ch. 2

by SILKsHEART on Sep 17, 2017
BDSM

(This is a two part story. This story is from the slave's perspective. The other part of the story is from the mistress's perspective. It is Training Slave Silk, Ch 6, by norma jeanne. It is probably best to read Training Slave Silk first and this second, however if you prefer you can read this one first.) * * * * * I woke stretching and yawning like a big...

Devil Takes Tessa

by l8bloom on Sep 13, 2017
Erotic Horror

With thanks to Darkniciad for all the red ink. * Tessa couldn't stop staring at the candy-red cock. It was red like the rest of him, red like the horns that protruded from his head. "You want it, don't you, little girl?" The Devil's mocking rumble was punctuated by a throaty laugh, the kind of laugh that would have made a bad girl squeal. But Tessa was a...

Late Night Coffee Ch. 01

by Estcher on Sep 14, 2017
Group Sex

I opted to revisit my first stories on Literotica. I wrote this story sitting alone in a hotel room. I decided to fix it up and finish the tale. - ETHAN WAS GETTING exhausted of the life of living in a hotel. He was away on business and had left his wife and kids back home. He was now on day fourteen and still had two weeks to go before he would return hom...

Trans-Formation

by dreadknots on Jan 20, 2020
Transgender & Crossdressers

This one is a lot more silly than my previous outings, but I think it's still a good read! Featuring guest appearances by chastity, dildo buttfucking, and hypnosis! Oh and turning into a girl at the end, that too. *** "Well," Tim said to the smouldering crater now taking up the majority of his backyard, "This isn't going to help the property value." An or...