Craigslist Stories

1,063 results
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Length
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Infinite Scroll

Search for a Lactating Relationship

by Leeaz383 on Dec 3, 2019
Fetish

Thanks for stopping by to read my story. This story is based on mostly facts, with names changed and details left out, to protect everyone involved. And of course: everyone in this story is way older than 18 years. No infringement is intended where some facets of this story reference materials I found on the Internet. If you are squeamish about having affa...

See You in RL

by Broadvue on Sep 14, 2017
Erotic Couplings

I was spending my evening like I did most evenings when I didn't have much to do: searching the web for great porn videos to jerk off to. As a late 20's man, I hardly think that is revelatory for anyone. I had a few choice sites I typically used where I could stream free videos and be reasonably sure I wouldn't get a computer virus. But this time, I wasn't f...

Louise... Slut at Last Pt. 02

by avengerfive on Jan 11, 2018
Loving Wives

After I pressed "Send" on the email to Les (who would hopefully soon be my wife Louise's new Master), the seconds ticked by at a glacial pace. It was already late afternoon when I sent Louise's contact information and weekly schedule to a man I'd only just "met" on craigslist. Soon, it was 5:30, and time for me to be heading home. But I didn't hear back from...

Last Minute Crossdressed Sex

by Lovinhose on Sep 14, 2017
Transsexuals & Crossdressers

I like to write and share my experiences with the world, and I prefer writing about REAL experiences, thought at some point, as in the past, when I hit a 'dry spell' and have no true story to write, I will write a piece of fantasy fiction. I am happy to say, however, that this story, while nothing special, IS TRUE, and I am happy to share it with you all. Al...

My First Couple

by sactofunseeker on Aug 31, 2017
Group Sex

I found myself once again reading the "Casual Encounters" section on Craigslist. You know how it goes, I'd been married for 25+ years and while the sex is okay, it is kind of the same most of the time. Some kissing, some touching and rubbing then I go down on her or we 69 until she cums then I climb on in missionary or do her from behind, fun but still kind...

Adventure on CL

by Pantyhoseheels on Apr 14, 2020
Transgender & Crossdressers

This is a mostly true story of the first time I revealed my secret side to another person. My name is Colleen, secretly. I have crossdressed most of my life. It has always been my little secret. But as with most people, I have had the desire to try being with someone else, and to share my secret. I began to occasionally check Craigslist, looking for that...

Bicurious and Married?

by Pirate_Guy on Sep 12, 2017
How To

So, since you clicked here, it's entirely likely you're one of the many married guys on Lit who are on the horns of a dilemma: You're straight, but you're really curious about the idea of sucking a big hard cock. Maybe you get turned on by the "pals go camping and get sweaty in the tent" stories. Perhaps the steamy tales about manly blowjobs in the health c...

The Ad

by tedsgirl on Sep 13, 2017
Erotic Couplings

Patti walked into the playroom and saw Ted watching something on the laptop. "Are you lookin' at porn again???" she asked teasing him. "Who me!? Never!" he said as she went and sat down next to him on the sofa. There on the screen were two men and a woman. The woman was sucking one cock and the guy getting sucked was sucking the other guy off. "Doesn't thi...

Alex Tests Sarah Ch. 03

by Alexandsarah on Sep 16, 2017
BDSM

Chapter Three - From the perspective of Alex I opened the web browser and went to CL.com. I'd already thought through our scene friends and none seemed like the right fit for Sarah's training tonight. Some newbies might be fun to play with. But it had to be a challenge, or it would be a boring swing session. We aren't swingers. I hated the pretend submissi...

What Craigslist Got Me!

by SissySlutPrincess on Oct 13, 2017
Transsexuals & Crossdressers

I had been crossdressing and playing by myself for years. A simple fun way to pleasure myself and satisfy my love for all things girly. I just needed more being from a small Ohio town made it tough to actually find someone to share this leisure with. Everyone knew everyone so no one wanted to get caught, but me! I decided to check out Craigslist. I posted a...