Up Mine! Let’s Resume Anal Training

I think we may need to return to anal play. It’s probably time to get back to BDSM. Apparently, my sex drive is connected to my bottoming. Maybe we could resume anal training. Mrs. Lion, at one point, set a goal of being able to peg me. I had to learn to accept the motion of a dildo moving in and out of my ass. That is very difficult for me.

We tried training me to accept pegging by inserting butt plugs and dildos of increasing size. We thought that my problem was being able to accept the diameter of a dildo. We reasoned that by giving me “practice” by inserting increasingly thicker toys, I would learn. That didn’t work. I accepted the larger toys, but when Mrs. Lion moved them in and out, it was too much. Then I learned we were using the wrong approach.

It turns out that the needed training isn’t just stretching. It’s accepting, removing, and accepting again. I read that the most useful training for pegging is slowly inserting and removing a butt plug over and over. The butt plug’s shape is an ever-increasing slope, getting wider and wider until it ends in a square shoulder topping a thinner stem. When inserted, the slope stretches the anus. Then, when the shoulder passes the opening, it suddenly closes. I find that an uncomfortable sensation.

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When the plug is removed, the anus must stretch wide to accommodate the shoulder and then shrink again as the plug gets narrower. It’s this forced change in diameter that prepares the anus for pegging. Larger plugs can be used as training progresses. We tried this for a short time. It was very uncomfortable at first, but I began to learn to handle the plug’s in-and-out motion over time.

I want to start this again. I think a goal of pegging makes a lot of sense. It provides anal stimulation, which is sexual, even though uncomfortable. It gives us a goal. And, if Mrs. Lion wants, she can even wear a strap-on and peg me that way.

Doing this represents work for her. She isn’t always up for it. Maybe training me on a regular schedule would help her form good habits too. She’s never been very good at consistent BDSM, and I’ve never wanted to face a regularly scheduled anal activity. It might be something positive for us both. We both tend toward the course of least resistance.

Anal play is more difficult for both of us. I don’t particularly like how it feels, and Mrs. Lion has to get up, fetch toys and lube, etc. Simple CBT is quicker and easier. I think we need to expand our play. I’m sure I will be sorry I said this, but I think some consistent rear entry is valuable for us.


  1. Perhaps if you do it right, it will give some new sensations.

  2. My wife and I have done some anal play on me over the years and I have always responded with “we need to do this more often!”
    Unfortunately her libido is waning and as a nurse she finds anal play somewhat repulsive. She has pegged me probably 3 times and I would be happy to make it a regular activity. I frequently use butt plugs on myself and crave taking on a regimen of anal training and stretching. Like you said, I would probably be sorry I received that.
    As I get older, I have thought it would be a reasonable progression from penis play to anal play as my penis function naturally fades. Not there yet!
    by the way, I read the preview of your book and really enjoyed it, bought the book

    1. Author

      Sorry about the loss of libido. Thanks for buying the book. Please leave a review on Amazon.

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