Chatroom Stories

364 results
Orientation
Length
Source
Infinite Scroll
SmutMD: The World's Biggest Erotic Literature Search Engine.
© 2025 SmutMD.com

The Bookstore

by aaronsandler on Sep 13, 2017
Fetish

Aaron had been showing his wife off online for a few years. It started slow, with just some bikini shots with her face blurred, or faceless nudes, but over time he began to show more and more. He found groups and chatrooms that specialized in that sort of thing; guys who liked to show off their wife. And she was worth showing off. Even now, in her 30's, she...

Jackie, My Ex, Starts Her Adventure

by Beeman2005 on Sep 14, 2017
Loving Wives

This story and the others about my adventures with my ex-wife Jackie (not her real name) are all basically true. This first one took place about 20 years ago. My ex-wife Jackie and I first started involving other people in our sex lives back in the prehistoric days of the internet, when all there was were the chatrooms on good old CompuServe. Back then, it...

Choice Number 1 OR Choice Number 2?

by MarriedMindGames on Jul 31, 2019
Loving Wives

[NOTE FROM THE AUTHOR: In my humble opinion, the best way to get the fullest sense of understanding and even enjoyment from this story is to read it through from beginning to end, and then return to read it a second time. I promise, if you follow that formula you will experience many "ah-ha" moments that will make you smile and think and perhaps even discove...

Erlebnisse einer Schülerin im Onlineflirt

by Truthahn on May 31, 2007
Non-English (dated)

Hallo! Entschuldigt, dass ich weder meinen Namen, noch mein Alter verrate, aber was ich euch erzählen will ist ein bisschen heikel! Ich gehe nämlich noch zur Schule und möchte euch hier von meinen Männererfahrungen schreiben. Also: Alles fing an, mit diesem Idioten. Der war in meiner Klasse und ich war eigentlich restlos verliebt in ihn! Ich dachte er auch i...

Open in Reader

Leaky Lindsay

by thedukeofpuke on Dec 25, 2018
Fetish

When I met her, Lindsay was a 19 year old 5'2" 105lb bulimic goth girl with a black bob cut and dark brown eyes. I found her online, in an eating disorders chat. How did that happen? Well, I'd been starving myself for quite some time and I had decided to talk about it with people on the internet, and amazingly, I found that the subject was almost exclusively...

Heathyr Hoffman Topless Turds

by Mike_Yates on Sep 17, 2017
Celebrities & Fan Fiction

The sexy/petite/short-haired blonde/thirty year old Heathyr Hoffman from season 1 (2009) of the hit SyFy channel reality television show ghost hunters academy became lonely and severely depressed after her boyfriend of 3 years left her for another woman who he was having an affair with. After falling into a deep depression and vigorously masturbating and do...

Since U Been Gone

by JukeboxEMCSA on Sep 1, 2017
Humor & Satire

I sppose yo're a bit crios abot the way I type. To be brtally honest, I'm a bit crios abot it myself. I know that something's nsal abot it, bt I can never qite seem to figre ot what it is. It's not that I'm confsed, yo nderstand. Well, not as yo wold se the word 'confsed', at least. Bt I jst...well, it's a bit of a long story, bt if yo don't mind a bit of at...

Txt Msg

by principessa07 on Sep 14, 2017
Toys & Masturbation

how r u? Nicole stared down at the phone in her hand and wondered if it was broken. She hadn't heard from Dan in months, it made absolutely no sense that he would be texting her now. And yet somehow his number was there, on the "from" line. No matter how hard she tried to forget him, his number was forever burned in her memory. She had spent many lonely nig...

Chatroom Trick

by ukmaleslave on Sep 15, 2017
Transsexuals & Crossdressers

I couldn’t believe I was doing this, as I stood by her front door I struggle to find breath on a surprisingly clear day. It had started some months ago, and internet chatroom, boy those things can be dangerous. I had spoke to Mary almost every night, soon chats turned to sex then to fantasies. The difference was she only lived in the next town so when she as...

I Look Like Jail Bait-Blind Date Ch. 01

by ILookLikeJailBait on Sep 12, 2017
Mature

While pretending he was her Daddy or the long-lost grandfather she never had, Kimberly roleplayed with a stranger, a much older man that she met online. Something she'd normally wouldn't do, would never do, she'd never meet a stranger she met on the Internet in person. That's just crazy and a good way to put herself in harm's way. Yet, with them seemingly...