Well, not technically Chicago, but that's the region I posted in. 

Rewinding. I had a work trip coming up to Chicago and had luck on this sub once before, so I thought I'd try again. I put up a post looking to indulge in no-reciprocation pleasing of a lady. Nothing makes me happier than bringing my partner pleasure and I said as much in my somewhat wordy post.
I got maybe three non-bot responses, of which only one turned into sustained conversation. She was at the moment traveling to a southern state but would be returning home when I was scheduled to be in Chicago. The slight hitch was that she was about 4 hours from Chicago. I didn't know if I had the time to make the drive during my limited time there, but we got along well on chat and when she sent pics of herself, I knew I had to find a way. She was chatty, respectful, and sexy.

We went back and forth. She worked nights, I was 4 hours way and worked in the day. Luckily I had a whole day where I didn't need to go into the office and was determined to make it work. I found a hotel that let me check in super early in the day after her shift ended, made a reservation and drove down there. We met for breakfast at a diner, and when we hugged warmly the first time we saw each other I knew we were going to have fun.

After we checked in she showered quickly and came out in sexy red lingerie. We had chatted for a week prior and over breakfast and her openness made it really easy to get comfortable with her. Our bodies melded together as I admired her form and kissed her all over, paying special attention to her lovely, shapely breasts, and going back up to make out with her. Her ass was a perfect handful as well and I grabbed it periodically. I laid her on the bed and started with a back rub, alternating between my hands and kisses. Eventually I laid beside her, turned her over in a spooning position, and started exploring her nether regions with my hand inside her thin panties. She was, unsurprisingly, very very wet. I smiled, kissed her, and put two fingers inside and curled them up. I played with her clit, rubbing around it and then on it. And thus began my discovery of how to please her with my fingers and mouth. I built her up with my tongue while her thighs were wrapped tightly around my head, and she eventually came with my fingers inside her and my mouth on her clit.

We had the day together, but she needed to get some sleep before her next shift the same evening and I had to work remotely. We alternated between her napping/me working, more fingering, and spooning tightly against each other until she had to get ready to leave. It was blissful and comfortable and slow.

We parted ways and then I drove back up in rush hour traffic, reminiscing about a wonderful day with her. It was a fantastic experience and I am so lucky to have met her.

Verification pic and hopefully she will comment below!