Craigslist Stories

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Making Out in Hotel Room

by Evergreen1963 on Jan 22, 2020
Erotic Couplings

I was going on yet another business trip. I always get lonely and horny on them. Even though I'm married there's something about both being away from home and not getting affection at home that makes my hormones kick in. And so I put a post on Craigslist for the city I was going to for a dinner date followed by cuddling, kissing, caressing and making out,...

Missed Connection Ch. 02

by Bizzy_Bish on Sep 12, 2017
Interracial Love

"I just don't think it's a good idea, that's all I'm sayin," Sean said as Kassidy pried her remote control out of his grasp. "I heard some weird shit about people who meet online." "I'm a big girl, Sun-Sean, I can take care of myself. Plus, technically, I didn't meet him online, I met him at the grocery store, " she replied, changing the channel. She kind o...

I Love My Nerd Pt. 01

by Nerdlover89 on Sep 13, 2017
Romance

I lay motionless, breathing heavily on the bed. I look to my right and see the man I had just made love to, and I start to wonder how he had pressed all of the right buttons to create the best 1st date of my life. It all started with a Craigslist ad. I had just recently moved to Minneapolis, MN, leaving my family behind in California. That always throws e...

Craigslist Adventures 03

by PorscheKaru on Mar 12, 2019
Transgender & Crossdressers

I had such nice, vivid, lifelike, sexy dreams again last night. Having had not one, but two sexy dick sucking encounters last night must have made me so horny. The dreams I had were so life-like, so real, felt like I was there. I woke up in all my sexy lingerie that felt so erotic and sensual on my body. I pulled out my laptop. I needed to orgasm. I love w...

The Christmas Party

by WhiskeyIsGood on Jan 31, 2018
Transsexuals & Crossdressers

So I meant to have this up for Christmas but, I got kinda busy with holiday shopping and all. Anyway, I hope you all enjoy it. Better late than never. * It was Christmas Eve. Being a single 30 year old man, who didn't keep in touch with much of my family, I had no intentions of sitting inside that night. It had been a rough year. Stressful even, with lots...

Good Deed Gets Blowjob In Return

by wildp on Sep 16, 2017
Mature

I had been divorced for a little while now and was still cleaning out my house. Trying to get rid of everything that reminded me of my now x-wife. I had been selling things on Ebay and Craigslist. If I could not sell it then I would put it on Craigslist under the free section. The free section is what ended up making this story. The first thing I ended up g...

Daisys day out

by sed42 on Mar 23, 2015
Erotic Couplings

Daisy is a Canadian teen girl who just moved to Springdale in the U.S. She stands 5'4", weighs 100lbs, has shoulder length blonde hair, and c-cup breasts. Daisy is at home alone today. Her family drove to their old place six hours away, to pick up the rest of thier belongings. She stayed behind with the excuse that she would start unpacking. But since t...

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True-Life Confessions of a CD

by Nils Huim on Nov 25, 2017
Transsexuals & Crossdressers

November 3 My hole is sore. But it's a good kind of sore. It feels s-t-r-e-t-c-h-e-d. More on the reason for this in a minute. Sex-wise I had a good day yesterday—one of the best ever. I invited three guys over to my house and two showed. (The third emailed me later saying he'd fallen asleep. "Are you available tomorrow?" "NO!") For fickle Craigslist, espe...

Craigslist Adventures 01

by PorscheKaru on May 21, 2018
Transsexuals & Crossdressers

Disclaimer: this is a series of stories I started a few years ago, I now realize Craigslist personals are dead but I wanted to write about all my crazy adventures to re-live them and share with everyone. They are my true real life encounters from the past, as well as a few from the present that happened before the service shut down. I hope you enjoy, it wi...

July Diaries Pt. 01

by clear88 on Sep 13, 2017
Exhibitionist & Voyeur

July 3, 2015 My birthday was last week. It was a fun weekend, but I started thinking as one does around birthdays... I've been single for years at this point. Honestly, I am pretty happy in general, and I'd much rather be single than with the wrong person or in a bad relationship. Still, it was nice to be with someone I really liked. I need to be honest ab...