Awkward Stories

44,618 results
Orientation
Length
Source
Infinite Scroll

Alice Takes a Cruise Ch. 02

by BobbiR on Sep 16, 2017
Novels and Novellas

It was difficult to believe that only a week ago I had been sitting in the drab lounge of my mother’s drab house in a drab grey suburb of London wondering if there was ever going to be any excitement in my life. I was already thirtyone years old, single and so little experienced in the ways of the world I hadn’t even had a boyfriend since leaving college ten...

First Cum, First Serve Pt. 02

by dreadknots on Jan 23, 2019
Sci-Fi & Fantasy

A sequel! This one has transformation of not just a gal but also a boy! If you don't like femboys and shemales might as well turn around at this point cause there's gonna be dicks, let me tell ya. Oh, and the standard cadre of weird fucking perversions: lactation, mind control, transformation. You know: totally normal things to get a boner over. Enjoy! **...

Ally - Born To Dominate Ch. 06

by sex4every1 on Dec 24, 2019
BDSM

A lot of readers wanted to know what it's like to be Ally's boyfriend. Well, my name is Roger and I am here to tell you all about it. I'll first give you an overview of what my (sex) life was like before I met Ally, then I'll share with you a very special story from the very beginning of our relationship. I am a fucking loser; this is especially so, now th...

Crosswinds Ch. 04

by Teagan_Cascade on Dec 24, 2019
Transgender & Crossdressers

Author's note: Contains elements of incest. ***** Maddi breathed a sigh of relief as the blue minus symbol came into view. She tossed the pregnancy test in the bathroom wastebasket and folded her arms as she contemplated. From her seat on the toilet, she took her time rolling her brown tights over her tapered legs. "This is crazy." She whispered, rubbing...

Her Daughter's Private Tuition

by Cleevedreams on Nov 18, 2019
Mature

Having just retired from a career in teaching, and being a single guy in his sixties, the world was my oyster. I was assessing my options. Should I move house, should I travel, should I write? Maybe do all three, I could do anything pretty much. There was nothing further from my mind than teaching, until that phone call. Brenda was a recent colleague in the...

Fantasy Woman

by imhapless on Feb 4, 2020
Loving Wives

I, Brian Davidson, was a late bloomer. All through High School physically I was a boy, not a man; while I had a cute face I was short and chubby. It wasn't until my first year in college that I started to mature, but then it was as dramatic a transformation as any that my doctor had ever seen. By the time that I graduated college I was nine inches taller, se...

The Sisterhood of Slaves Pt. 05

by sarobah on Apr 22, 2020
BDSM

Dramatis Personæ "We shall not cease from exploration And the end of all our exploring Will be to arrive where we started And know the place for the first time." — T.S. Eliot, Little Gidding A whistle at noon signaled the end of the Saturday shift. The construction crew locked away their tools and secured the site before heading back into town; except...

A Cuckold Fantasy Realized

by sweetlucky12 on May 4, 2020
Loving Wives

Susan was feeling stressed and anxious. She was tremendously busy at work and at home her kids were driving her crazy! Her loving husband Tom could feel Sue's stress building. Her 40th birthday was approaching, so as a gift he planned a trip to celebrate. They would leave the kids at Tom's parents' house and take a long weekend trip to California. Tom and S...

Lessons Learned Ch. 01: The Class

by M8dOvGlaz on Dec 2, 2019
Exhibitionist & Voyeur

April 27, 2020: I have submitted an edited copy of this story to Literotica. Thanks to andyinoz for giving chapter 1 and 2 a lookover for me! Chapter 1: The Class It was my last semester at college in 1999. It would be my last full term to complete my bachelor's degree, and then it would be time to move on to grad school in another state. I was getting a b...

There and Back Again Ch. 006

by ElyssaCousland on Dec 3, 2019
Celebrities & Fan Fiction

Chapter Six: Preparations I woke, at home, stiff and sore in my own bed. I was surprised to find that I was dry, no indication that I had soiled myself while unconscious. And my pockets were largely empty, so most of the things I left in the pack must still be there. Good to know. My bladder did feel full, but not painfully so, and I rolled out of the bed...