Lion wrote about his latest ruined orgasm and suggests that he be punished for ejaculating without permission. Number one, we never had an agreement about that. I can’t just retroactively decide to enforce a rule I make today for something that happened days ago. Number two, I think he’s looking for ways to be punished.

After our eight hour drive yesterday (we always forget to factor in stops along the way) as we were setting up the RV, we had a leaky hose. Lion asked me to look at it to see where the leak was coming from. I did and started to tell him. He interrupted. When I snapped at him and finished my assessment of the leak he told me to check again because it couldn’t possibly be leaking from that point. This remark is dangerously close to something my ex would say. I rechecked the leak and, no surprise, it was leaking from the same spot I saw it the first time.

What Lion didn’t realize is that I brought some of his Good Lion and Naughty Lion coupons with us. As soon as we were all set up I wrote out a Naughty Lion coupon for his remark. He says he’s sorry he ever made them. Of course he wouldn’t be saying that if he had earned a Good Lion coupon first. He was to get four hard swats as punishment.

Then we went to dinner. Lion had oysters. Squishy things that don’t look appetizing at all. He said they were great. He followed that up with rare prime rib. It was still mooing. A few hours later, he had what I assume is food poisoning. He was up half the night in pain.

Needless to say, he didn’t get his punishment. Nor did he get his orgasm. As he said, it’s not the end of the world. I didn’t tell him we’ll try again in December. Things happen that delay plans. I think the reason I was so upset the other night, other than the fact that he was disappointed, is that I don’t have much to offer except my word, and I went back on my word that he’d have an orgasm.

We still have a lot of work to do. I’m sure I’ll disappoint him again. He needs to handle it better. I do too. But we’re in this for the long haul. We’ll figure it out.

[Lion — I didn’t suggest punishing me for not controlling my orgasms. I said that it seemed fair that I take some responsibility for it. I did say that others who have been trained this way did get spanked or something when they had an “accident”. In this case, I am not looking for punishment. I just think I should help by holding back.Negative reinforcement seems logical to me.]

Thursday’s ruined orgasm upset both of us. Mrs. Lion wrote about how it hurt her to disappoint me. It brought back feelings of inadequacy that were not far from the surface. I felt childish disappointment at losing my prize. I was wrong, of course. Her teasing was amazing. I was flying from the way she played me like a violin. She really has learned how to stimulate me like no other, including myself. So, when that stimulation went just a bit too far and I could feel myself squeezing involuntarily, I knew we had passed the point of no return.

I was sad and it showed. I could see that she was upset too. Things didn’t go the way either uf us wanted. Both of us overreacted. After all, one orgasm lost isn’t exactly a big deal. It wasn’t as if Mrs. Lion was going to say, “We’ll try again in December.”

All that really happened is that my wait was unexpectedly delayed a day or so. No big deal. In fact many keyholders do this sort of thing on purpose. So why all the pain? I think it is because we are both trying so hard to do the “right thing” for each other. I  have no small amount of guilt about selfishly wanting to bring this chastity fantasy to life. I had hoped that it wold turn out to be fun for Mrs. Lion. So far it hasn’t. She does it just because she knows I want it.

I realize that even after nearly seven months of this, she has yet to find anything in it that touches her. What a selfish person I must be to want her to continue. But I do. Why am I such a brat to openly express disappointment when all Mrs. Lion was doing was trying to make things more fun to me? Why should she feel badly and believe she did something wrong? She shouldn’t. The simple fact is that she has been doing everything right. She has been working hard to make chastity work for me. If I could love her any more for doing this, I would. But the simple fact is that I love her with all my heart with or without chastity.

She’s said that one reason it has become important to continue is that our chastity activities have forced her to stay focused on our sex life. It has for me too. This is a very good thing for us. While we are inseparable and absolutely mated for life, we both can let sex slip. The difference in our libidos makes it easier sometimes to avoid sexual contact rather than deal with those differences. A lot of that is my fault. Her lower interest level always made me feel like I was selfishly intruding with my “needs”. It became easier to deal with them myself than bother her.

The difference now is that we made a deal, a contract if you will, that we will pursue forced male chastity as I envisioned it for two years. This gets me what I have wanted, but it feels to me that so far I am the only one who is benefiting. This has to change or we will both find ways to feel badly about more and more.

Another realization that I have had is that perhaps Mrs. Lion should hold me responsible for unauthorized ejaculation. Other keyholders expect their males to only come when given permission, regardless of the stimulation. I’ve never tried this. Maybe I should. On the other hand, this can become just one more work item for Mrs. Lion with no real reward for her. I don’t want to add any more problems to what has become a difficult process for her that isn’t even pleasant.

Sounds like we should just stop, doesn’t it? I don’t think so. We both get some positives too. We are waking up our sexual feelings for each other. Under the guise of turning me on, Mrs. Lion has asked me to make her orgsm twice in the last month. For her, that is a very frequent schedule. I love that and I know she is having fun.

There may be light at the end of the tunnel. I expect we have a lot of work to do to get there. If she felt able, I deserved a hard spanking after that ruined orgasm: 1 for coming without permission and, 2 for upsetting my lovely lioness. Maybe she owes me another “Naughty Lion” coupon for that. I certainly didn’t do myself proud at all. I feel terrible about making her feel inadequate and sad. That’s unforgivable.

Every time I want to give Lion an orgasm I think I should just do it. You know, the long buildup and then the orgasm. But now it feels like there’s pressure to edge him first. Tease him and edge him every other day. Tease him further than last time. There’s always the possibility of a ruined orgasm. Then there’s the possibility of whatever we had the other night which was more than a ruined orgasm. Then there’s last night which was beyond that. I pushed him way too far and he didn’t get his orgasm that he had been anticipating for eleven days.

He’s disappointed. I’m disappointed. We tried again about an hour later, but whether it was really not possible or he was just too upset, I couldn’t get him hard again. Maybe we could try in the morning, but Lion has never been a morning sex kind of guy. In this case, that really sucks because we’ve got a seven hour drive ahead of us and he’s wild and he’s disappointed and I’m mad that I disappointed him and now I’m awake at 5 in the morning writing this and you can imagine how much fun this drive will be.

The worst part is that for a few minutes he thought I was actually trying to push him too far. Why would I do that when I know he’s been waiting eleven days? Why would I do that when he specifically said he didn’t want to come a day early because he was looking forward to “a big send off” for our last trip? I should have just played with him enough to get him excited and then given him his orgasm. Nothing fancy. But I feel pressure to make it fancy. I don’t want him to have a boring orgasm after waiting so long and with him anticipating “a big send off”.

He’s been telling me how much better I am at edging him and how interesting it feels to have multiple ruined orgasms. Do more. Do it more often. He says I’m starting to enjoy things. I think I’m just getting more confident that I can do what he wants and not hurt him. And then something like this happens and the rug is pulled out from under me again.

I’m sure he’ll read this and think we should just stop or that I want to stop. I’m just irritated that I disappointed him and for what? So he could have a better, less vanilla orgasm? Yeah, that worked out. I know I can make him come tonight, but it was supposed to be last night. And I was already thinking about making him come tonight anyway.

I think I’ll go back to my less confident way of doing things. In some ways I feel safer with my insecurities.

in control
Mrs. Lion has evolved and taken more and more control of me.

Over the last six months Mrs. Lion has evolved from a reluctant keyholder who just wanted to do what I want to a lioness in control of my chastity. This evolution hasn’t been easy for her and I am very grateful for her efforts. It seems that with each passing week she seems more comfortable as her role as my keyholder. For example, she plans my waits and sticks to her plans. Twice in recent days she has told me that she wants me to please her. How cool is that? She writes that she does it as an alternative to teasing me. That’s fine. I just love giving her pleasure. Wednesday night I was allowed to give her several orgasms. I had my cage on and my penis was pushing hard against the bars.

She’s also publicly set goals for herself: teasing every other day, longer waits with added or subtracted days, enjoying my frustration, more discipline, etc. All of these challenge her since she isn’t generally a results-oriented person. She made it clear that I will be caged for a very long time. She said that the cage helps her to stay with the focus on our sexual communication.

Most significantly, she seems to have learned to enjoy the results of her actions. She laughs at my grumbles and appears to genuinely enjoy seeing me frustrated at the edge of orgasm. She also seems to like reminding me that I have to wait when I let her know I am horny.

All this seems to signal that Mrs. Lion is having some fun with my chastity. That is what I had hoped would happen. As she gets more comfortable and continues to realize that I am happy and grateful she is “torturing” me, I’m sure she will expand her activities and control. Mrs. Lion read this post and commented that she isn’t sure that she is enjoying my response as much as grateful she can do it with less trepidation.

I look forward (and dread) the expansion of her activities. I am all too aware that my anal training has just started. I wonder if Mrs. Lion will set a date by which I must accept her hand? That may be the one element that Mrs. Lion might consider changing. Goals are wonderful, but are improved with a target date.

I am also sure she will expand her disciplinary activities. I remember when I first asked her to spank me; those first swats were just little pats on my butt. Now, she has no problem making me squirm. I expect she will expand her spanking and shocking and begin enjoying my discomfort. Once she starts liking my reaction, she will push harder. I want her to do that. After all, a month or two ago, Mrs. Lion felt badly when she edged me and saw my frustration. Now she enjoys seeing me squirm and react when I get just to the edge and she stops. I think that if she disciplines more (she really doesn’t need a reason) she will also enjoy my discomfort. I  know I will.