This was way back when Cragislist Casual Encounters was a thing, and I was really reluctant to look for sex on the internet, so I started slow. It was a post inviting a woman to come and watch me masturbate. It had always been a fantasy of mine and just thought that was a low key, easy way to start.
To my surprise, I received a response that same night from a woman named April. We chatted back and forth several times and set something up at my apartment the next evening. She had shared a picture of herself and I thought she was average, but had some nice big breasts. Most of all, she seemed very eager and turned on at the idea of watching me.
We had set a time for her to come over, and I had started masturbating and edging a while before that so I would be really horny and turned on by the time she rang my doorbell.
When that moment came, I was very excited, a little nervous and curious at how this would play out. I remember we sat on the couch and had some pretty easy, natural conversation. When there was a lull, I asked if she was ready to start. She nodded and said yes. I slowly slid my hand into my pants and started to make myself hard (I didn’t want to reveal it until it was).You could tell she was really turned on just watching me play with myself without being exposed.
Then, I finally pulled out my cock, much to her delight. I lubed it up with some oil and stroked it for her in several different positions, eventually standing in front of her with my cock right in her face. She absolutely loved it and eventually took her hand and stroked it with me. She took off her top and exposed her tits for me and let me cum all over them.From there, I was hooked. I met up with April a dozen times of so before we lost touch.
She eventually sucked my cock and always took my cum on her tits or with me shooting it over her face and in her open mouth.
Over the years, before CL ditched its casual encounters section, I met close to 100 women for all sorts of sexual activity. Lots of masturbating, but also a lot of sex too. Fuck, I miss those times, lol.
Source: reddit.com/r/gonewildstories/comments/113ela5/mf_my_first_experience_with_craigslist_casual