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I wanted to share my first time having Anal Sex and the first time writing so be kind! It is also a true story so if anyone has any feedback or wants to hear more, please let me know. -----I'm not sure where my obsessions with anal sex came from but it had increasingly begun to monopolise my fantasies. Jul 14, 2016 · My first anal experience. One woman revealed that her first anal experience was an accident. She said, "We were going at it doggie style, he pulled out and in his haste to plunge back in he hit the wrong hole.