Hotel Meetup With Benefits

In my 20's I went through a professional MA program at a university with a cohort of students who then dispersed across the country, but some of us stayed in touch via email for a decade or so afterwards. One of these was Nance, a small, thin, dark-haired Jewish lady a few years older than me. I barely knew her in school, but we met a few times over the years due to professional conferences. We actually never attended the same one, but once she hosted me for a night while I was driving from my work location to a distant conference, and a few years later she stayed at my place when one of her conferences was in my city. On that occasion, a remark about enjoying massages led to my giving her a much-desired backrub, but we didn't go any further. She was very attractive though and we got along well, even though we weren't exactly each others' type.

A few years later she was planning to go to another conference in a distant state, but I happened to be passing through it on the way back from a family event, so we planned to meet up. I parked at her hotel and we hung out in her room for a bit, both just eating leftovers and snacks we had lying around or brought with. I was planning to drive a few more hours to stay at a friend's house for a few days before the final leg of the trip home, but at some point we started discussing our dating lives and she mentioned that she had gone out with one guy for a while who wouldn't give oral sex, which was essential for her. I expressed dismay and said I would have trouble with a woman who didn't like receiving it, since I loved giving it so much. This perked her attention and we talked around the topic for a few minutes, until she ventured further that the way she really liked it was sitting on a man's face. I laid back on her bed and basically invited her on, and she said "seriously?"--but she said it not laughing, but seriously herself. "I am serious--if you pass this up you'll always wonder what it would have been like." She made it clear that she wasn't interested in intercourse tonight, which I totally agreed to, so in a couple minutes she striped down but left her socks and shoes on, which I found enormously erotic. Then she sat on my face, arms bracing herself against the wall, and stared down at me intently. I reached up to her wonderful legs and got her in just the right place to start lapping at her well-trimmed pussy. For about ten minutes the only noise was her occasional terse directions about speed and position as I learned what she needed, then she started shouted "oh-ah...oh-ah,..oh-aaaaaah " and wiggled around a bit before lifting off to recuperate. Then she asked if I could go again, I said yes so she descended for another licking and this time in about five minutes she came again, after which she fell to the side to relax. She commended my efforts and kept looking at me with surprise and relief, being especially glad that our friendship wasn't ruined with what might have been sub-par sex. She then asked if I wanted to stay the night, which I did since it was getting late, but I did ask if I could get any help cumming myself. She quickly volunteered, and within minutes I was sitting in a chair with this naked (but still shoed) little woman kneeling in front of me, my dick out of my zipper. She remarked on its impressive size (I think I' m average, but she apparently had been getting smaller ones in recent years). She sucked me skillfully, but asked me not to cum in her mouth; I let her take charge and it didn't take long for me to start ejaculating, mostly on her face but she did catch some in her mouth, which then dribbled out--apparently she was ok with some, just didn't want to take it all down at once.

After that we slept pretty soundly, waking up to a cuddle session which soon turned into a 69, which ended with us both cumming again. Sadly, I didn't hear much from her after that and our professional paths haven't crossed since, but I was glad to have once tasted her delicious little pussy in the middle of an otherwise pretty exhausting trip.