I tried online dating and met the queen of anal

A few years ago- I posted an ad on Craiglist in the men-seeking-women category just to see what would happen. I don’t remember the exact words, but the post had a link to a picture of my cock letting girls know I was looking for a warm pussy to release my load in a no-strings-attached situation.

Honestly, I didn’t expect much and my inbox was soon filled with random messages from mostly other men wanting to see more pictures. A guy even offered me $100 to let him suck me off.

One email seemed legit- the girl’s name was Jessie and she lived nearby telling me she recently broke up with her boyfriend and just needed to have fun with some dick. I sent her a selfie, asking her to send me something so that I knew she was real. Right away, I get the response. She was sitting in front of a mirror naked from the waist down with her pussy spread holding a card with Jessie spelled out and the day’s date.

That message got me rock hard and I texted her right away my address to set something up. That night, I couldn’t believe it. Jessie (~22F) shows up at my door in a coat, hiding a long dress. I was nervous as the closest thing I had done like this was a one-night stand and this hot girl just shows up at my door to fuck. She had the classic hipster vibe, with straight black hair, dark eyeliner and some tattoos on her arm but what really got my attention was her amazing body around 5’6 120lbs with perky boobs.

It was a bit awkward at first, as we moved to the living room. I offered her a beer but she grabbed my bong and bag of weed on the table. Packing a couple of bowls, we just had some small talk about the weather getting blazed pretty quickly.

That’s when she got up and started to undo her dress. Playing along I took off my pants sitting on the couch. Right away she takes my dick into her mouth, with a pretty aggressive blowjob using both hands and pushing it down the throat. Trust me when I say, that was exactly what I needed.

At some point, before I could cum, she stopped and told me I needed to return the favor. Her pussy was beautiful. With a nicely trimmed bush, I was fascinated by the tight lips and pink color. I was more than happy to taste her cunt that first time, licking the clit with pleasure while using my finger to rub inside towards the g-spot.

From there, it really became a marathon session- we fucked on that couch in every position. doggie/ cowgirl/ missionary- the feeling was amazing the explore every inch of her body but she wanted more. From her purse, she pulled out a vile of oil and told me she wanted me in her ass.

This was my first time doing anal. From the sitting position, she squatted up and slowly tried to slide down my shaft. She had to bounce on my dick head for a minute for it to loosen up, but soon enough I was all the way inside. It felt like a death grip around my penis with the shaft tightly squeezed by a rink.

Each time she levitated up and down, I could feel myself getting ready to explode. Giving her that load was an experience I’ll never forget as it completely wrung me dry and got my whole body shaking. Jessie sat there still as my dick went soft, holding her arms around my neck with her boobs in my face telling me I was a good boy and did a great job.

Cleaning up, we smoked some more before Jessie left that night. Over the next few weeks, we started having more regular casual sex. She would randomly show up at my door and demand I fuck her, with the anal creampie always the main event.