The Craigslist Freak - Sex Stories

The Craigslist Freak

This story happened about a 3 months before my last story, its the summer of 2010, Im miserable, lonesome, and feeling down about just about everything. That means its time to hunt some strange on craigslist. An add appears in women for men, its title reads something like "seeking man who likes anal play." I like anal play, though I had never done it with anyone else, so why not give her a shot? I send her a message with a pic of me using some of my toys, I fully expect her to: 1. be ugly, 2. be a man, 3. never respond to me, or 4. be a real live woman. Well she was #4, and she was a 40 year old cougar with an amazing body (pics are in my profile under old craigslist hookup). After driving out to meet her we kicked back, had a few beers and exchanged some small talk. Then she made her move, she scooted up next to me and slid her hand between my legs saying "I want this." She opened my button down shirt, licking the center of my chest, working her way down, unfastening my pants, unzipping me, then she slipped my cock into her mouth. She sucked me until I was hard then leaned back looked up at me while stroking my cock and said "Nice." She stripped, laid back on the couch and presented herself to me saying "I want you to eat out, make me cum!" So I fell to my knees, sucked her clit into my mouth, began flicking it with my tongue as I worked her in and out of my mouth. She moaned like a filthy whore, bucking into my face covering my chin with her wetness. I slipped a finger ...

... into her and immediately she said "More!" so I slipped another finger, then another, soon I was using all four of my fingers in her cunt, she was growling with pleasure, scratching my shoulders and neck as I brought her to orgasm. When she finally came, she told me to bend over. As I bent over I thought "This is it, the first time someone does something to my ass!" She takes my butt plug, lubes it up, and works it into me ever so slowly. "That feel good baby?" she asks, I moan out "Oh god yes!" She's working it in and out of me, stretching my hole, then she pulls out the plug and starts working me with her fingers. She fits 4 in with ease, she says "Ive never fisted a guy before, I might be able to get all of my hand in!" She keeps stretching my wider and wider, working her hand back in forth, until finally she slips her whole hand in. "Holy shit!" she says, "Thats fucking cool!" My eyes are rolling back in my head, Ive never been this stretched and full at the same time, Im leaking cum and I dont care, this is amazing! She grabs her cell phone and takes a picture of her hand in me, I hand her mine so that she can do the same but she tosses it aside. Now she grabs my massive black dildo, "I want you to use this on me like you want me to use it on you." She spreads herself open and I slide the huge cock into her waiting hole. I start working her harder and faster "Yeah, is that how you want me to fuck you!?" I keep fucking her, she screams out in ecstasy as she cums on the huge ...