Craigslist Stories

1,063 results
Orientation
Length
Source
Infinite Scroll

Cody Becomes Chloe Pt. 01

by Southernstud97 on Sep 16, 2017
Transsexuals & Crossdressers

Please note this is my first story and I will continue writing if I get some feedback and people enjoy it. Thanks for ready, hope you enjoy! ***** Cody was not your typical high school student. He rarely hung out with friends, never went to any parties, and never really talked to girls. His parents believe that it was only a phase and that next year at col...

My First Time with a Man

by chastr on Jul 2, 2018
First Time

This is a true story of my first time with a man. I was 68 years old and had been using various objects to insert in my ass while masturbating. I started with household items, such as candles, brush handles, etc. as well as fingers. I then moved up to carrots, small zucchinis and cucumbers. I learned that having something shoved up my ass made my orgasms mu...

She Was Watching

by jbulldog on Sep 11, 2017
Exhibitionist & Voyeur

This one happened to me recently - It was Friday night and my usual online surfing just wasn't doing it for me. It had been weeks since I had sex with my girl. . . I had heard about Craigslist, and went surfing around. I couldn't believe what I saw! So many people posting for so many different appetites! I found one advertising for anonymous and NSA oral...

Camping Alone Has Huge Advantages

by Lovinhose on Sep 16, 2017
Transsexuals & Crossdressers

This is another true story, probably the last one (for now) worth writing about. I have been fucked while dressed 19 times to date. Not nearly as many times as I'd like (as I type this though, I have an ad posted on Craigslist again and hoping for another memorable story to relay to my readers), 9 of which were with a regular I had for a short time, and was...

Meeting Master, Meeting Myself

by sdbnnc on Sep 17, 2017
BDSM

Before I met Master, my life involved very few connections or interactions with other people -- I lived almost completely in my head. I attended college and earned a degree; I worked hard at my chosen profession. I made and kept a small group of very close friends. I even maintained close family ties. But my true self was kept secret -- even from the public,...

Craigslist CD Hookup

by Lovinhose on Sep 16, 2017
Transsexuals & Crossdressers

I have been crossdressing since I was a kid. I started out with a pair of my mother's pantyhose, as most other crossdressers start out the same way. Once you get bit by the bug, you're hooked. This is my first story, but I have so much to tell that this certainly won't be my last. All of what I tell you here will be 100% true. I will not dramatize or sensati...

The Help Ch. 01

by Rosebella on Sep 14, 2017
BDSM

January 5th, 2011 Dear Alissa, I lost my job three weeks ago and the apartment manager just taped a 3-day notice on my door yesterday. I have no idea what I'm going to do, but I'm hoping this guy from a craigslist post calls me back. He needs a live-in maid. That should be easy enough and I'll have a place to stay until I get back onto my feet. I'll let yo...

Casual Encounter

by davion2308 on Sep 16, 2017
Letters & Transcripts

"Dear Jeanette, Hi, it's Kristy. I wanted you to know that this is my first week of living on campus. I'm so excited to be at college now! I know you aren't going to make it out here and I'm sorry, but you still got into community college and that's cool. I'll be home next week for the weekend and we'll still hang out. This place is insane! I realize I'm so...

Craigslist Adventures 02

by PorscheKaru on Oct 24, 2018
Transgender & Crossdressers

I woke the next day, so satisfied from my previous night's encounter. I'm still wearing the stockings, panties, and bra from last night. I had nice sweet and naughty dreams so I woke feeling so horny. I grabbed my laptop so I could put on some porn. I want to see a beautiful sexy blonde girl sucking a hard, fat, long cock until it cums into her mouth, then...

CD Gets Fucked while House-Sitting

by Lovinhose on Sep 16, 2017
Transsexuals & Crossdressers

This is a true story that happened recently. I also recently submitted a four-part, runaway-imagination complete fiction story, hope you enjoyed. For anyone not familiar with me or my stories, here's a brief background. I'm middle age, white, a little overweight (hidden well with the right garments), and a married bisexual crossdresser who LOVES getting scr...