Omegle Stories

9 results
Orientation
Length
Source
Infinite Scroll

Jackpot

by AndrewEros on Sep 16, 2017
Exhibitionist & Voyeur

For any straight man who occasionally visits websites like Chat Roulette or Omegle, there are two things you hope you're going to see but know, in your heart of hearts, that you're almost never going to happen across: a willing woman or an exhibitionist couple. But that doesn't stop thousands of people clicking and clicking and clicking through with hope and...

Chat with a Girl

by bemybetch on Sep 16, 2017
Letters & Transcripts

You're now chatting with a random stranger. Say hi! Official messages from Omegle will not be sent with the label 'Stranger:'. Strangers claiming to represent Omegle are lying. Stranger: hii You: heya Stranger: asl You: m Stranger: f You: 18 Stranger: 18 You: uk :P Stranger: oh shit im frm uk too You: ohaha You: awesome :D Stranger: where bouts...

Omegle Slut

by jessiemonkey on May 13, 2020
Letters & Transcripts

I went on omegle and this is a chat I had. This is all true, but I have edited it to get rid of spelling errors. We are both over 18 and were consenting. After this conversation I asked if she was okay with me posting this and she agreed. I hope you enjoy it. You're now chatting with a random stranger. Say STAND WITH HONG KONG AGAINST THE CCP! You both lik...

Cybersex, Woman Centric

by draviddr on Sep 14, 2017
Letters & Transcripts

You're now chatting with a random stranger. Say hi! You both like sleep. Stranger: I'm Sara. I'm 21 You: hi sara I'm Sam 27 Stranger: Nice to meet you Sam Stranger: Can't sleep? You: yeah You: not tired enough :) Stranger: Don't you hate that feeling? You: I do - hoping someone on Omegle can tire me out Stranger: haha the best way I can fall asleep...

A Random Stranger

by geonisis on Sep 14, 2017
Humor & Satire

Hey everyone, as this is my first post I would love if everyone really let me know what you think. I am open to all comments but probably won't respond unless it is constructive criticism, so without further ado I present to you my first work. Hope you all enjoy it. You're now chatting with a random stranger. Say hi! That was how it started, I've only rece...

"Like It?" "I've Seen Bigger."

by leBonhomme on Sep 16, 2017
Letters & Transcripts

Omegle, Chatroulette, Franceroulette, a Russian chat site, and no doubt others, have uncovered -literally - many persons' willingness to expose themselves and have cyber sex. Sometimes the chats are interesting; most of the time, they follow a fairly boring standard pattern. The following is an attempt to suggest that chats could be wittier. When line...

Finding Picasso Ch. 06

by Jason_NYC on Oct 6, 2020
Exhibitionist & Voyeur

On the ride from the Bois de Vincennes back into Central Paris, Runa and we detour through an old residential neighborhood that somehow eluded Haussmann's 19th-century wrecking ball. We stop at a cafe with a Belle-Epoch facade and Art Nouveau lettering. "Can you imagine?" I ask as we sip cafe expresso. "Cezanne could have sat here? Or Gauguin? or even van...

Taking Mom's Place

by Sissy_Sammi_ on Jan 31, 2018
Transsexuals & Crossdressers

Editor's note: this story contains scenes of incest or incest content. ***** *All characters are 18+ years old. This is the first entry to this story, so if you like it I can continue it. ***** Jack walked back into his old room with his suitcases in tow and couldn't help but feel the shame and sadness that lingered there. He knew that his father was ex...

The Dark Window

by the_lost_one on Sep 13, 2017
Erotic Horror

Foreword -------- Dedicated to the random omegle guy/girl. Your input made it possible for me to finish the story! I hope you read this! Thank you very much for your help. ^_^ This is my first ever attempt at writing erotica, you will notice that my skills are still raw and needs much polishing. I would greatly appreciate all input you can provide. ---...