About a year and a half ago, I was on a week-long business trip -- orientation for a new job that was ultimately a bad fit. So, being by myself in an unfamiliar town, I figured I'd see if I might meet someone local to go out and get to know the area a little.

I matched with her on an app and explained my setup. She said she'd be happy to meet up and see if we click so we can have some fun - neither of us was really looking for anything serious anyway. So we met up at this trendy seafood restaurant that was absolutely delicious. We had a couple of drinks with dinner, and the conversation flowed really well. When we asked for the check (I may or may not have billed the meal to my firm heh), she leaned forward and said I'd be welcome to head back to her place. I said I'd love to.

A short while later, we were on her couch in a cute little townhouse. We were sort of vaguely role-playing the idea of having a glass of wine, but really the focus was on each other. She stretched her legs out across my lap, I massaged her calves and slowly worked my way up to her thighs. She straddled me and pulled her dress off over her head to reveal black lace lingerie before starting to unbutton my shirt - I was still in my daily business casual from the office. A few minutes of grinding and making out later, she invited me up to her room.

She sat on the edge of her bed and I stand in front of her. She slowly curled her fingers around the waistband of my boxers and pulls them down. My cock, which she knew had been hard for a good while already, playfully bounced back up after the tip got past the fabric of my underwear. She grabbed the base and wasted absolutely no time putting it in her mouth. She didn't aim for depth or speed here, which I appreciated - rather, she focused on a more sensual touch, using her mouth on the tip and a hand on the shaft. It was delightful, but I had other things in mind, so after a short while I pushed her onto her back and straddled her torso. With my right hand I reached back between her legs, and with my left I pressed lightly down at the top of her chest, just below her neck. With my right hand, I circled my fingers around her clit, slowly inching closer to it, occasionally sliding across her labia, occasionally sliding between them to wet my fingers a little. With some exploration, I realized she reacted most intensely when I would slip two fingers in and curl them on the way out. So I focused on that movement. I upped the pressure and the pace, all the while holding her down with my left hand as she squirmed and moaned. Then she tugged my left had up toward her neck. Understanding the signal, I closed my fingers around her throat and started to choke her, my right hand still working her g-spot, until her voice caught in her throat for that moment orgasm sets in and stayed frozen until the intensity broke and she let out a long, throaty moan.

But we weren't done yet. I got off her and said "get on your hands and knees." She was eager and obedient, even if it took her a moment to collect herself and actually comply. I slipped a condom on, held her at the hip with one hand and guided my cock into her pussy with the other. I like a slow pace in doggy, at least at first. It's more sensual and I can appreciate the feeling of it a lot more. But, being who I am, I was staring at her asshole the entire time. So not too long into fucking her, I asked, "do you like having your ass played with?" She breathed a "yes." I asked if she had some lube, and she crawled over to her bedside and pulled out a small bottle before returning to her position on her hands and knees, this time with a little more arch in her back. I kept a slow pace while fucking her, so I could focus more on what my hands were doing to her ass. I spread her cheeks wide with my hands, and with lube on my right thumb I started drawing little circles around her ass. Every so often, I would circle with a bit more pressure. Each time I did that, I pushed a little bit harder. She was incredibly receptive. Within just a minute or so, she was enjoying my thumb sliding in and out. "How are we doing?" I asked. "That feels really good," she said. "Good girl."

I pulled back from her, re-applied some lube, and started working my index and middle fingers into her ass. Again, she was immediately receptive; she started rocking her hips back against my hand. I asked her how she feels about anal; she said it's been a long time but she does like and would be down to try. By this point I was pretty confident she was ready for my cock, but I know to take my time here. After a lot of lube, I pressed the tip of my cock against her ass, built a bit of pressure then waited. I let her ease it into her, but where normally I would have expected a slow build up to my full length, this time she was able to slip me all the way in almost immediately. Seeing her confidence, I grabbed her hips and took control. She was moaning softly and I was breathing deep and slow; I savored the tight slide of her ass across my shaft. I would pull out entirely now and then just to feel the tip slide back in, to her vocal delight.

A few minutes later she looked at me over her shoulder and said "I want you to cum." Now, normally, I'm all about cumming in a girl's ass. But this time, the condoms she had on hand weren't ones I was used to. The were a bit thicker and I wasn't really building up to climax. I explained as much, and I asked her if I could take the condom off and grind up on her. She seemed enthusiastic about the idea. So, with dramatic flair, I pulled the condom off and cast it aside. With another healthy amount of lube, I put my cock flat against her asshole and starting to rock my hips. This sort of grinding is such a turn-on for me. It feels great and it's an anal tease, so I am all for it. In no time at all, my breath got heavier and I started grinding harder and faster. And just as I was about to cum, I brought my body down on top of hers, laying her flat onto her bed, and with a final few thrusts, this time with her cheeks fully pressing against my cock, I came all over her back.

We took some time to just lie there before getting cleaned up. I got dressed and she put on a robe to walk me to the door. We parted with a little kiss and a mutual hope that we could meet up again. But then six months later, I quit my job, so I don't think that's going to happen, unfortuantely haha.