I dated a woman for a few months and though the relationship was never very good. We were both in our 30s and hit it off in the work environment and were definitely up for sex to put it bluntly. Though I liked her wicked sense of humor and smile (and adorable bottom), most of our day to day conversations were quite negative, competitive, and sometimes very bitter, arguments. The only place where we never argued or actually never even talked was in bed when we were naked. It just hit me the other day that I can only think of one time when she said something to me that was 100% sweet, gentle, in a seductive erotic way.
She said, "You touched me in a new place" in a very sultry whisper. This was just after I had, for the first time and I was quite nervous, toucher her anus.
I had always been fascinated by her little round bottom (she was quite athletic) and has caressed it many times but anytime I got close and played near her crack, she pulled away or turned over onto her back. This one night she was lying on her stomach as I massaged her back and eventually just caressed her bottom. Because she seemed so relaxed and I was so determined and aroused, I knelt over her with my face just above her cheeks and pulled them apart with my thumbs. She had the tiniest, palest, hairless little hole I have ever seen. I couldn't believe I was finally looking at it. And I leaned in and touched the tip of my tongue to it and very slowly moved it around in circles for I don't know how long. God it was good. She didn't flinch or move but kept breathing heavier and heavier. I started toucher her pussy and then her clitoris with my thumb as I rimmed her. Gradually I began to push the tip of my tongue in a bit, until her anus relaxed and I entered it slightly. As her breathing became quiet moaning, I pushed in more, until I was fucking her ass with my tongue. Not very deep, maybe just an inch, but I was enough and it was so damn hot.
Eventually she came, rolled over onto her back, and pulled me onto her. As we lay there silent, she finally said something. "You touched me in a new place." I said back to her, "I liked it."
Unfortunately we broke up only a couple weeks later. Before we did, our bedtime activities included a lot more rimming (only me of her) and also me fucking her bottom with my finger, as deep as I could, in and out slowly. I suppose if we had stayed together it was only a matter of time before we had anal intercourse, and I'm sure at some point I would have wanted her to return the favor, rimming and fucking me. But I'll never know. As good as the sex was, it was otherwise an unhealthy relationship. But wow I have some great memories of her.