The date was a normal date with a couple we have known since the beginning. They both like the anal play. They know I do too, but this was the first time that it happened. During playtime my playmate was going down on me and playing around down there. I simply looked at her and said, “I am okay with whatever you want to do.”
She started out slowly, teasing my anus. That in itself was interesting. I can’t recall anyone ever touching me there aside from myself and toys. It felt good. She paused for a moment to grab the lube. That made it even better. She kept rubbing gently. Slowly she began to apply more pressure. At the point I was almost involuntarily pushing back. I needed her in me. Needed to be penetrated. If she noticed my pushing back she didn’t seem to care and continued forward at her own slow, agonizing, titillating pace. Her finger crept inside me eventually reaching my prostate.
Now I am not new to prostate and anal play. I have been exploring that by myself to some degree or another since I was probably 14, but having someone else in me was excitingly different. Toys are well they are toys and while some of them are very good at their job they are exceedingly different from fingers. My own fingers are well, my own. That in itself takes makes it different. Not to mention the fact that it is really awkward to touch your own prostate. I definitely enjoyed having my prostate massaged by her fingers and look forward to more such experiences in the future.
This is one of the many reasons I really love the life I live now. Exploring things, new exciting things, without fear or shame. Before this event I had always said I would like to try pegging, but I wanted to try it with Anne first. While I would still love her to peg me and be into all this, it may be that she just never will be. I am leaning now towards maybe being open to exploring it with someone else. Maybe.
