I have been thinking that fingering the asshole is a prelude for an anal sex. It had happened once with a woman I met in a music show. I was in my late 20s and she was about 7 or 8 years older than me. We had sex in our first date, and I realized she was a bit cheeky. Then, in our following encounters, she would sleep in my place, which would give enough time to fuck her and try out new ideas. In our third or fourth encounter, she was lying on my bed, and I started playing with my index and middle fingers close to her asshole, caressing and getting closer and closer. Then, I put my index finger inside her ass. She didn’t complain at all. She even started to scream a lot, without taking too long to reach an orgasm. Early in the morning, she jokingly said something like: “you were very cheeky, sticking your finger up my ass”!
In the very next encounter, we had anal sex. I had played with my finger in her asshole, and then I started to play with my cock, rubbing in her crack and close to her asshole. This time, she simply helped to put my cock in her asshole. So, anal sex would become our “normal” routine. Often, she would quickly reach an orgasm, sometimes multiple. Most times, we would have anal sex in the spooning position, but once I grabbed her hair, and, with my cock inside her ass, I led her to a table next to the bed. We fucked both stood, while she had her hands on the table. She screamed a lot, like always. In the following day, she would text me: “All our dates were great, but this night was probably the best one”!
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