Many years ago, I had anal sex with a man I was very much in love with. I am now getting involved in a new relationship. My new lover knows that I have had anal sex before, but he does not know how long it has been. My question is: since I have not had anal sex for a long time, will we have to start from the beginning?
–Going Back to the Backdoor
Besides saying “a long time,” you didn’t specify exactly how long it’s been since you’ve had a cock up your ass. A year? Five years? Ten years? If it’s been more than a few years, then you should start slowly. Begin with lots of foreplay and lube and work your way up to one finger or a slim toy, and don’t go any farther than that. Next time, you can experiment with two fingers. You want to re-introduce the pleasures of buttfucking to your ass in a gradual way.
Don’t think of it as a chore, but instead use it as an opportunity to re-experience the first time you ever had something in your ass. You and your guy can revel in the excitement, the slight resistance, the de-flowering of that tight little hole. Relish each new step when your ass is able to take a little more. The body does have memory, so I suspect that it may take less time to build from fingers to your new lover’s dick, but everyone is different. Listen to your body, honor its boundaries, and take it as slow as you need to.