(I've been lurking this sub for awhile now, and there's tons of hot stories on here, so I felt like I'd give sharing my own a try. I hope you guys enjoy it, and it's not too bad.)
This happened around 9 months or so ago; I was feeling a bit lonely, and hadn't had sex in months, and Tinder didn't seem to be working very well for me at the time. So out of pure curiousity, I decided to try looking through Craigslist ads. After weeks of wading through ads that turned out to be spam bots or prostitutes, I was more or less ready to give up.
I saw an ad for a woman a few years older than me, looking for a hook up in the near future. I decided to send her a picture, and she happened to like what she saw. We exchanged more pictures, and wound up talking for a few days, and feeling each other out.
on one late night she asked if she could come over, and I was free and more than happy to oblige. She had long black hair, tanned skin, and she was curvy (which I'm into, so that worked for me.)
I'd like to say I was suave and had her clothes off within minutes, but I wasn't. I had never done anything like this before, and had just come out of a long relationship, so I was nervous and awkward at first. She admitted it was her first time hooking up with a stranger like this too, so that made me feel a bit more comfortable. We talked for about half an hour, just breaking the ice. Eventually, I summoned up the nerve to kiss her.
Her lips were soft, and tasted of cotton candy. I couldnt help but imagine how they'd feel wrapped around my shaft, as I explored her body with my hands. We got off the couch and I led her into my bedroom.
It was dark, but I could still make out her lovely figure as she disrobed and climbed onto my bed. We resumed our kissing, while I slid my hand between her legs and began rubbing her clit. the sound of her moaning against my lips had me as hard as a rock, and she must have noticed, because she traced her way down my body with her lips, and proceeded to give me some of the best oral I've ever recieved. It was wet, slow, and rhythmic at first, and she knew I was loving every second of it; the more I moaned, the more she picked up the pace. I had to stop her before I came right in her mouth. I had her bend over while I stood up and slid the condom on my hard shaft, before I slid it inside her. She moved her hips back to meet every thrust, throwing herself back on me hard, while she moaned and rubbed her clit. I smacked her ass and held onto her hips as our bodies smacked together over and over. Before long she was climaxing, clenching all over my cock while i thrusted into her, and it wasn't long before I joined her in ecstasy, and erupted as well.
We laid there for a few minutes and talked. She had to head home and get some sleep. (at this point it was more like the wee hours of the morning). She thanked me for helping her fulfill a fantasy, and I walked her out.
We hooked up a few more times after that, and it was always a fun time. I'm definitely glad I took that chance.
Source: reddit.com/r/gonewildstories/comments/3qdh65/my_first_craigslist_hookup