Backdoor Fun

You can always tell how interested I am in sex by what I write. I’m sure I will not shock you if I tell you that I’ve been thinking about sex. Even though we are celebrating Unlocktober, we haven’t quite kept up with our every-other-day pace of orgasms. Saturday night, we started late and while Mrs. Lion worked valiantly pumping my penis with her hand, I got very hard but I just couldn’t get past that plateau. She’s resolved to keep trying.

Meanwhile, my thoughts have been drifting rearward. My antasies are remembrances of my own anal experiences. For a while, Mrs. Lion was working to expand, so to speak, my anal horizon. She was using a combination of fingers, butt plugs, and ever-increasing-in-diameter dildos.

For me, anal penetration creates an interesting set of sensations. First, the cold, gentle caress of lube being applied around the rim of my asshole. Then, a few seconds later, the gentle-yet- firm press of my lioness’ finger as she parts my puckered hole. That first intrusion is a little painful. I have to breathe and try to relax as she penetrates me. Mrs. Lion prefers using her bare fingers. If I ask, she will wear a glove. I know she prefers skin-to-skin contact.

Once she gets her finger fully inside me, she often leaves that there for a bit to allow me to get used to it. Then she will move her finger in and out. That motion is a combination of uncomfortable and exciting. I know my next anal visitor won’t be as easy to accept. Next, she will fill a little syringe with lube and insert it in my ass, releasing the lube inside. She may repeat this. When she’s satisfied that I’m slippery enough, she will lube the tip and body of a medium-sized butt plug. Then, with no further delay, I feel it pressing against me, sliding inside and stretching me. Initially, it’s not too bad. Before long though it starts to hurt.

Often, that means the lube had rubbed off and I was hitting a dry spot. Mrs. Lion will partially remove the plug, add a little bit more lube and continue pressing. Eventually, she reaches the shoulders of the plug where the diameter becomes much smaller. At that point I feel a sharp pain and then breathe a sigh of relief that the plug is firmly inside.

Often, this is where things end. She’ll leave the plug parked in my ass for a couple of hours, and then remove it and wipe away the lube. Other times, she will leave it in for a little bit and then remove it. She will then use one of my dildos and replace the butt plug with the silicone penis. This is followed by a slow in and out as she lets me get used to the feeling of being fucked.

This is always uncomfortable. If she leaves the dildos fully inserted it will begin to feel comfortable after a minute or two. Moving it in and out doesn’t really feel good to me. It isn’t so bad that I want her to stop. I just wish it would feel better. She picks up speed. It’s very intense for me. Sometimes she pulls the dildos all the way out and then immediately pushes it back in. At first, I really hate that sensationn. After she persists I start to get used to it. She picks up more speed pounding harder and pulling the dildos completely out after almost every stroke. I grunt and work hard to stay open and accepting. Sometimes I can’t and I ask her to slow down or stop. She usually listens to me.

In a way this is a problem. She reasons that she is doing this for me. So if I don’t like it and ask her to stop, she should do it. The reason that is something I would like to see changed is that I want to learn to be able to take it. There have to be times when I really want that discomfort to end. I know that if it does, I’m not going to learn. It would be easier for me if I didn’t have to avoid asking to stop. If my protests were ignored as a way of helping me grow, I think it would be a better experience for me.

We used to work on training me to take Mrs. Lion’s entire hand. We stopped. I would like to try that again. I read that some people use butt plugs a little differently. Instead of inserting them and leaving them in place, they use them in a similar way to how Mrs. Lion uses the dildos: they move it in and out forcing the anus to expand and contract with every stroke. This has to feel horrible at first, but I can see the value in this exercise. Forcing the expansion and contraction over and over is a very good way to train me to be able to relax more. If I can learn to just stay open, the in-and-out motion could become enjoyable. More importantly, learning to relax the anal sphincter muscles will make it much easier for me to accept Mrs. Lion’s hand.

I had a friend back east who was seriously into fisting men. No, she never had a chance to try fisting me. We talked about it once in a while and she told me that it normally takes about 45 minutes with a beginner. She didn’t use any tools. She just worked with her fingers. She claimed that by patiently and persistently working in one finger at a time, she could always get her entire hand up any man’s ass. I can see how it could take at least 45 minutes. My limited experience is that it takes patience to give me the time to relax at each step.

I don’t think I’ll ever be one of those guys who can get off while being pegged or fisted. I doubt I’ll even be able to get hard while that’s going on. But there’s something emotionally satisfying about having to learn to accept whatever Mrs. Lion chooses to insert. Even though I know I will be uncomfortable, I always feel closer to her after each session.

4 comments on “Backdoor Fun
  1. Jimbob says:

    From my experience I always go soft while being pegged if I’m not caged. Mistress C usually likes to see me leak first while caged though. She never has a hard time to get me to cum while pegging me with the wand while caged. If I’m free a lubed hand gets me right at attention fast. I will say that if have strongest orgasms when she strokes me while pegging. As soon as I orgasm I’m ready for it to be done though. She likes to get me right on edge then let me dribble while she continues to peg me which only produces a ruin orgasm then repeat. It’s something as straight male I enjoy and have grown right fond of because the power exchange is incredible.

    • Caged Lion says:

      So far, I don’t get hard when anal action gets going. Occasionally, I will be hard for a while but when the anal intensity grows my arousal goes away. That doesn’t mean I don’t want the anal action. It just means that my sexual focus seems to get distorted. I’m not claiming it will always be this way. Perhaps, in the future I will be able to get off the way you do.

  2. mrbillsails says:

    I fantasize that as my ability to get an erection fades with age that my sexuality will shift to my ass. I do enjoy when my wife gives attention to my ass and she has pegged me a few times. I liked that a lot and wish it was more common.
    The last two orgasms I had were as she stroked my penis while finger fucking my anus. Totally mind blowing. Maybe this is the path to the new normal?

    • Caged Lion says:

      We have lots of nerve endings in our asses. I have wondered if Mrs. Lion fingered me while she masturbates me, if after a while I would get aroused simply by having something up my ass. No need to worry about losing erections. Generic Cialis and Viagra are available at great prices.

What do you think?