Chatroom Stories

364 results
Orientation
Length
Source
Infinite Scroll

Beginnings of our FLR and a Cuckold

by JCDubois on May 11, 2020
BDSM

Once upon a time not so long ago in a land not so far away there lived a couple just like any other. Well, there were a few differences that made them unique. After a few years of not being able to get pregnant, the wife blamed the husband and began to regularly berate his masculinity. At first, this was done in bed after sex she would share how disappoint...

Dream

by REGG60 on Sep 13, 2017
Romance

I wrote this short story many years ago when I help run a local BBS, it was one of the first BBS's at least in our area that had chatroom capabilities, if I remember correctly we had 6 phone lines, before that women were few and far between in the use of any BBS, before chatrooms most women couldn't understand what their husbands and boyfriends saw in the co...

Roll Me Away

by Aradia Zayn on Sep 17, 2017
Non-Erotic

I start to reflect upon the two-year anniversary of the death of my love while driving to my favorite spot. I pop a CD in and Bob Segar begins to sing Roll Me Away. I get to the spot at the lake and roll the windows down on my car so that I can still hear the music. I sit on the trunk of my car watching the water ripple and the sunset, reminiscing about what...

How to Break All the Cybersex Rules

by goddessinjapan on Sep 12, 2017
How To

Ever wondered how nice, normal people wander into the world of cybersex? Ever wondered what cyber is, how it feels, why people bother? Here's my personal journey, written at the time and annotated later! I hope that you enjoy reading and get a new perspective. I realize that some of my advice/ hints go against the grain, but, hey, I broke the rules and end...

Lilac's 18yo Friend: Moniqua Chats

by NonStopFunGuy on Sep 19, 2017
Exhibitionist & Voyeur

After two decades of chatting with horny women on the Internet, the best orgasms I ever had occurred just this past summer. I had three intense, almost painful ejaculations from the hottest, sluttiest girl I'd ever met, online or in person -- a petite, pretty black 18 year old named Moniqua. Wow, could that chick take a big cock into her tiny pink pussy! Le...

A Virgin's Awakening Ch. 1

by SubTopical on Sep 17, 2017
BDSM

It was a comment from a stranger in a BDSM chatroom that started the whole thing. She'd been lurking in chatrooms for months now, drawn to the lurid discussions of acts straight out of her fantasies. She never spoke up herself, though, still not really believing that there were so many others "like" her. With each passing day she became more impatient wit...

For Services Rendered

by Pen_is_Mightier on Aug 19, 2017
Exhibitionist & Voyeur

(Best read while soaking in a warm tub) * The boredom of her life had simply become too much. The kids had all left the house for college and her days were seemingly endless. Sure, she had tried to cultivate some hobbies, but nothing seemed able to maintain her interest. She had begun to spend hours surfing the net, mindlessly following links until she los...

Aimee

by Challenged on Nov 11, 2019
Romance

*Author's Note* This is a short story based on a recent experience here on the site. And yeah, all the character specific info has been modified to avoid identification. *laughs* I will apologize now, for any typos I missed. Remember, all comments graciously accepted! Enjoy! ****** Aimee The Paths We Choose 1 She originally met him in her usual cha...

Lissane Saga Ch. 01: Meeting Mistress

by Broken_Serenity on Sep 14, 2017
BDSM

Lissane came home from another day of tiring work. She worked in a place worse than hooters, men could be shameless. Though, she felt no sexual attraction to them she didn't dislike them. The blonde kicked of her shoes before walking down a carpeted hall towards her room. "I'm home.." she said, though she lived with none but a spoiled white-haired cat named...

Directed: His First Account

by IFOnle on Jan 7, 2018
Exhibitionist & Voyeur

Written under the Direction of and Approved by IF. ***** She ['Katie', if that was her name] returned from the Ladies, slid elegantly into the nook - and smoothly across until the warmth of her hip was pressed to mine. "Thank you," she turned, biting down quickly on my earlobe, then taking up the fresh glass of wine I'd ordered in her absence. She was att...