Awkward Stories

44,618 results
Orientation
Length
Source
Infinite Scroll

Jeanie's Lamp Ch. 04

by dgirlanonymous on Jun 1, 2020
Transgender & Crossdressers

Music blasted from my car speakers as I sped down the street, the deep bass of the rap song I was listening to shaking the frame of the car around me. I didn't much care for the music itself, but I was unreasonably proud of the aftermarket sound system I'd personally installed and couldn't resist showing it off every now and then with the loudest, most bass...

Summer Days Ch. 07

by BrazenHorse on Jun 1, 2020
Exhibitionist & Voyeur

Christina, Ashley, and Justin spent the rest of the afternoon sitting around the pool, relaxing in the sun. Justin remained naked the entire time while Ashley ended up putting her bikini top back on. She wasn't yet as comfortable as Justin was being naked, especially in front of Christina. "Anyone want to order a pizza?" Christina asked the group as they c...

For Their Pleasure Pt. 04

by DanteDidIt on Jun 1, 2020
Transgender & Crossdressers

The next few months went by in a whirlwind. I met so many new men and was opened up to so many new ways of seeing the world. Plus so many different ways of being fucked and feeling pleasure. It was incredible what some of these men could do to me and what they wanted done to them. I never could have believed the depths of the male sexual mind until I became...

Black Sheep Boy Ch. 03

by Biguy5774 on Jun 1, 2020
Transgender & Crossdressers

All characters are eighteen. *** Over the next week, Alex could hardly keep himself from fucking Robin. They did it whenever they got the chance. They hung out almost every day of the week, and anytime it was just the two of them it wasn't long before Alex was cajoling Robin into sex. And he usually ended up succeeding. It didn't matter so much that Jamie...

After It Happened

by jealouscuck on Jun 1, 2020
Interracial Love

This is the fourth chapter of the adventures of Charli, Stan and Lucas. I should have organized in Chapter form, but I didn't anticipate this to be this long. Please refer back to the earlier chapters, all containing the word HAPPENED. I apologize for the inconvenience. Chapter 4 Once Lucas realized that Stan was interested in his story about his sex life,...

Satisfied at Last

by SKArgo on Jun 8, 2020
Group Sex

NOTE: Some words and sentences are in italics to indicate a character's thoughts. Please retain that formatting * Satisfied at Last A vacation threesome we'll never forget The first time I saw Melissa I nearly sliced off my finger. The ad agency where she'd been promoted to social media manager rented out the restaurant where I'm a line cook for a party....

Tessa and the New Guy

by SteveLengAndrew on Jun 8, 2020
Erotic Couplings

Part 1 Not for the first time, Tessa reflected that Americans were quite...prudish. In Europe, it was neither uncommon nor frowned upon for even married couples to stray outside the relationship (within reason, obviously.) Given the square-jawed, blue-eyed, gorgeous (but married) new guy at work, Tessa currently found the American prudishness especially fru...

How it began Ch. 03

by ghost12_spirit on Jun 8, 2020
Exhibitionist & Voyeur

I hope that you enjoy this third chapter of "How it began". I have enjoyed writing about the adventures of this character and reading all of your comments. The story picks up immediately after being caught naked in the middle of the road. ----------------------------------- The sun shone in a strange window. A pleasant breeze fluttered through the bright...

Librarian Finds Long Overdue Love Ch. 13

by RVon on Jul 13, 2020
Fetish

December 14, 1987 Single, middle-aged and bespectacled Angelina Lione may look the part of the prim, proper and sexually repressed, buttoned-up bibliothec, but she's most definitely NOT your father's librarian -- at least not while in a lover's company. Blessed with a ravenous and unquenchable sexual appetite, Angelina's orgasms are so intense that she ofte...

The New Boarder 03

by PickFiction on Jul 13, 2020
Exhibitionist & Voyeur

All of my writing is fiction and the stories and characters are all products of my imagination. They were created for my fun and, hopefully, your enjoyment. Some of the events in the stories are not particularly condoned nor encouraged by the author but are there to create and enhance the story of the imaginary characters and their lives. Comments are always...