Craigslist Stories

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Crossdressing Playdate at the Lake

by montrealjane on Sep 16, 2017
Transsexuals & Crossdressers

At the end of the summer, I was lucky enough to have some playtime at the lake. I had been emailing and IM'ing back and forward with a girl that I had found on Craigslist. Craigslist is something of a lottery full of timewasters and scary people using many bogus identities, so it takes some time to filter out who really serious to get together and have fun,...

For Love of Doggy Style

by pullmeinside on Sep 16, 2017
Interracial Love

I came across a post on craigslist asking why men love doggy style so much. I felt I had a duty to provide some sort of explanation. I couldn't speak for all men, but I shared my own feelings on the subject and the impressions conveyed to me by others – shit my friends say. I was very detailed. I touched on everything from angle of penetration, feeling of do...

24hr Hall Pass

by Lamplight69 on Sep 13, 2017
Group Sex

Sam and I had been dating for about 3yrs and she became increasingly demanding in bed over that time. If I didn't make her cum before I left for work, she would spend the day eating my head about it. One day I literally just wasn't in the mood and left for work without even having sex with her, and the shit started almost right away. We were arguing about an...

Craigslist Chronicles Ch. 01

by Anarchist4life on Sep 1, 2017
Group Sex

In the fall of 2009 I put up an ad on Craigslist, not for the first time, asking if anyone wanted to help me lose my virginity. Sometimes it was placed in romantic m4w, sometimes in casual encounters. It wasn't necessarily serious, mostly a curiosity to see who and what type of responses I got. Kindof an interesting experiment. Over the months, some respons...

My New Life

by quietguyin_tn on Sep 16, 2017
Transsexuals & Crossdressers

I was married to the same woman for 30 years. Now on my own, disappointed, but committed to creating a life that I wanted. What do I want? Moving from suburbia, I bought a house in the city, surrounded by 30 somethings with tattoos and piercings. "WOW! This is different," I would mumble to myself over and over again. I could walk to restaurants and stores,...

Lock Your Phone

by Iamasissy on Sep 15, 2017
Transsexuals & Crossdressers

I am a sissy and I love it like most sissies I dream about belonging to a man to be owned by him. I fantasize about being outed and being forced to become a transsexual. I put out adds on craigslist NY looking for a Master. I take lots of pictures dressed, I take videos dressed saying my name is Karen I am a sissy and I want to become a transsexual for a rea...

We Both Fulfil Our Fantasy

by Gratefulone on Sep 28, 2020
Loving Wives

My name is Jeff and this is the story of the first successful MMF I had with my girlfriend Tae. While this wasn't that long ago it was in the day when you could find a successful rendezvous on craigslist. A little about us I'm an average size man with a little better than average size package. To describe Tae would be to describe an African American version...

Craigslist Meet

by Bobbirox2 on Oct 6, 2020
Transgender & Crossdressers

A few years ago, I was going through the local Craigslist M4T ads (while they still up and running - such a shame they got taken down). I found an ad that I was interested in and wrote the gentleman and told him that I was interested in getting to know him. We exchanged a half dozen or so emails and decided to hook up later that night. I had a delivery job...

Allie's Encounter on Craigslist

by allycd on Sep 13, 2017
Transsexuals & Crossdressers

Let me start off by saying this is a 100% true story. I know there's some that will try and pretend to be real but are in fact not. There's no real way for me to prove it, but nonetheless I just wanted to share my experience. About a week ago I posted an ad on craigslist "19 y/o Asian CD looking for a dominant top", asking for their pictures and stats. Aft...

First Time Exposed

by mauioutlaw on Sep 13, 2017
Exhibitionist & Voyeur

A few years ago when my wife and I started to experience a decline in our sex life, I turned to the internet as many men in my situation do. I did the usual perusing of nude websites, looking at pictures of porn stars and such but eventually settling into viewing real wives posted by husbands and boyfriends. I began thinking about posting my wife's photos bu...