Awkward Stories

44,618 results
Orientation
Length
Source
Infinite Scroll

Not That Kind of Girl

by Nevereverhere on Sep 13, 2017
Erotic Couplings

Daniel kept his left hand in his pocket while the woman standing next to him at the coffee shop flirted with him. A cute brunette, she definitely seemed interested in him, following him over to a ledge by the wall, trying to keep conversation going. Still unsure whether she'd be the kind to hook up with a married man or not, he slipped his ring off, picked...

Kiss the Bride

by RedBarnErotica on Sep 12, 2017
First Time

Amelia and her parents arrived at the church after a long wagon ride through the country, in the early morning. Waiting for them there was her future husband, William, whom she had never met before. The ceremony was short and simple followed by the regular Sunday service. The priest skipped the part about kissing the bride. This was not the wedding Amelia h...

Office Dating Policy

by Nomi_Furstenburgh on Oct 7, 2019
Transgender & Crossdressers

So, here I am. It's four in the morning and I'm sitting at the bar. We were having a special night. One of the staff, Gerry, was leaving us tomorrow. He was hired on as a curator at a museum in L.A. and would be leaving soon. As this was a special evening we had several of the performers do acts on stage that were not a part of the normal entertainment. Se...

My First Time in College

by Total_ROM on Nov 18, 2019
First Time

I did not, by any means, have the most exciting time in college. In particular, my freshman, junior, and senior years were characterized much more by studying and school anxiety than they were with parties, belligerence, and especially encounters with the female gender. Freshman year I lived in a 'pod' with three other guys, two of whom would go on to become...

Everything's Good

by MichaelFitzgerald on Jul 31, 2019
Loving Wives

I wrote this some time ago under another pen name. If you prefer not to read a BTB, you might like something else better. I knew it was going to be bad when two of the three detectives turned away from me when I walked in. There was a flat panel monitor on the wall rolling static on the screen. The one detective who would look at me told me to sit. We were...

The Widow's Club Ch. 01

by Jackobin on Nov 16, 2020
BDSM

[This story has many aspects and could have also been listed under the Mature and Fetish categories, among others. It has some references to bodily functions, so if that bothers you, I suggest you read no further. All characters in this story are well over 18 years old.] Millie reveals her perverse longings to Dotty who finds the ideal solution When Mrs. M...

Moonlight Saunata

by RaoulDukesAlterEgo on Sep 12, 2017
Loving Wives

We'd spent the evening with wine glasses in hand, naked in the Jacuzzi, under the starlit sky. Joy and Jason were married, but they'd gone through a rough patch and during that time Joy had been with another. Jason eventually realized that he was alright with Joy's escapades; in fact he was infatuated with the thought of her and a lover taking each other in...

Feet on the Ceiling

by BigWillie1314 on Jul 31, 2018
Erotic Couplings

With much appreciation to LarryInSeattle and his editorial toolkit. * *** * She had dated Kevin, my best friend in college, when they were in high school. They had broken up before he graduated, but this past year she had made the five-hour drive from her college several times to visit him over the weekend and party with other folks they both knew. She alw...

The Making of a Cuckold Ch. 05

by NotJustAHatRack38 on Dec 10, 2018
Loving Wives

As they all tried to regain some control of their situations, Michael's eyes stayed glued to the couple on the bed. Paul was coming to his senses, realizing that he had fucked Lynn hard with his full cock and cum in her unprotected womb, something he had been careful never to do before. Lynn was motionless on the bed, eyes closed, mouth partially opened. "O...

A Diary for Two Ch. 03

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

A very slow built story about a character's transformation from being entirely male, to having to accept his magically switching gender. There are sexy bits and they will be more frequent in planned subsequent chapters, but they are not the main focus. Please do not expect any quick thrill out of this story, but please make the most of the progressive deve...