Anal play (Page 38)

I think I may have tried to rush things last night. We started off with Lion on all fours. I used his clone dildo on him. Rather than stretching him, I wanted to get him used to the movement. He definitely needs more practice. It was difficult for him so we stopped fairly quickly.

Then we moved on to spanking. I started with my hand but I didn’t warm him up enough. Instead of getting him to his zone, it was painful. However, when he asked me to stop I kept going. Even if it’s painful I felt it was necessary for me to dictate when I stopped.

Although I flexed my muscle, so to speak, I consider the spanking to be a failure. I didn’t do what I wanted to do. I didn’t do what Lion needed. While it’s true that I am trying to train him, I am also trying to train myself. I need to be consistent not only with the amount of attention I pay him, but also the quality of it.

I’m not giving up. I’m sure I’ll get more training this weekend. Spanking in the sling is not the easiest, but it does offer wonderful access to his buns. We also have a spanking bench that hasn’t seen much activity in a while. I’ll have to correct that oversight. Sounds like another busy weekend for Lion. Too bad he has to wait till Monday for his orgasm.

I didn’t play with Lion last night. He was still basking in the afterglow of his orgasm the day before. Not that he wouldn’t have enjoyed anything I did to him. He just didn’t need anything urgently. Tonight is a different story. I’m working late but it’s a play night so I do have plans for him.

Actually I’m torn between using my new nubby paddle and plugging his butt. I could do both. I think it depends on how I feel later. If I have the energy I think he might get some red buns. A toasty tush. He always appreciates that. And it’s been a while.

The other night he said I could probably get the bigger Njoy plug in him. I bet I could, but it’s also been a while since he’s had a plug in there. I feel safer with the smaller one until I actually get him stretched a little more. So maybe he will get a butt plug tonight. And the rest of the week. And maybe on the weekend I can get him back in his sling for more of an anal workout. And then I bet he’ll be ready for the bigger plug. I know he’s thinking, “Yes, please!”

So tonight he will be a plugged Lion with a chance of red buns. I don’t think Mr. Weenie will be wild though. He had his fun on Sunday. He can wait another day or so to make an appearance. I’m hoping he appreciates the butt plug and spanking though. It’s nice when he tries to get hard inside the cage. Poor Mr. Weenie. Happy Lion.

For whatever reason, Sunday night has always been a rough night for me as far as sleeping is concerned. I’m thinking about everything that needs to be done in the coming week and what didn’t get done in the previous week. My mind won’t shut off. Last night I was thinking about Lion.

I’m afraid I’m disappointing him. I don’t make new rules. I don’t punish him when he breaks the rules I’ve already made. I’m not consistent with training. The only things I’m consistent with, aside from disappointing him, is that he is locked up and I play with him at least every other day. Keeping him locked up is a passive thing. Once he’s locked I don’t need to do anything. I’m good at that. But that may be the only thing I’m good at. I’m failing at being his keyholder.

So last night I was thinking about concentrating on short term goals. Yes, I’d like him to be able to accept my fist up his ass, but we’re not going to get there at the rate we’re going. This week, assuming he is a horny boy tonight or tomorrow night and has a nice big erection, I want to make the second Lion clone. Hopefully it will be a bigger, more accurate version of his Mini Me. And then I can use it on him. He should have anal training at least twice a week. Not always with his clone. Sometimes it will be with a butt plug. Pegging should be once a week so he gets used to the motion and the size. The butt plug will help stretch him. If I can maintain this training then eventually we can move on to bigger things.

I need to focus more on punishment. I hate it. He loves it. It’s what he wants/needs so I’ll do it. My short term goal is to be more consistent with enforcing the rules we already have. When I am consistent with that I can add more rules. And perhaps in the short term I can throw in a punishment or two just because he’s annoyed me for whatever reason.

In his post this morning, he says he thinks the shock collar would be useful to train him not to have an orgasm when I edge him. We can try it. I really don’t think it’s his fault when I push him too far, but he wants to get shocked so shock I will.

Now for the big one. I want to get my libido back. I’m not entirely sure how to do it except to do it. I’m hoping if Lion gives me orgasms then eventually I will start wanting them more and more. So my short term goal is to have an orgasm at least once a week. I know the mechanics are there. I know he can give me an orgasm. It’s a case of the body being willing whether the mind cares or not.

I know Lion will always want more. That’s just how he’s wired. He’ll find a new idea or toy and want to add it to our repertoire. And I’ll stress out about it because I’ll feel I’m not doing enough for him. Eventually I’ll give him what he wants. Or I’ll at least try to give him what he wants. I just don’t want to disappoint him.

Tuesday night Mrs. Lion decided to continue my anal education. It’s been a while and I am out of practice.  Before I went into the shower she placed the Boy Butter and a chrome butt plug and my “mini me” clone of my not-fully-engorged penis on the bed. She waited until after I took my shower and when I got out asked me which toy I wanted inside me. I asked her to make the decision and lay flat on my stomach. Soon I felt her fingers getting lube around and into my anus. This was followed by an object. At first I thought it was the plug; uncomfortable at first, then it felt good as it went deeper. This wasn’t right. A plug gets more uncomfortable since it’s width grows until it gets to the “shoulder” and suddenly narrows down. I don’t like the feeling when it suddenly narrows. This was different. It just felt good. I asked what was inside me and Mrs. Lion said it was my mini me.

I liked how it felt. Being fucked by my own penis actually felt good! In the past, partners had told me that my penis was perfect for anal sex. I figured it was because I’m not that big. Now I discovered that they were right. I like how it feels. She gently pegged me for a bit and when it started getting uncomfortable, I asked her to stop. This is the first time in ages I really enjoyed something up my ass. I want Mrs. Lion to do it again soon.

After the pegging, we relaxed and watched TV. When we were close to bedtime, Mrs. Lion mentioned that she had my key out on her nightstand. I suggested it was an awful waste not to use it. She smiled and unlocked me. I had already accepted that the anal attention was the end of this play session, so it was a real surprise that there would be more. Mrs. Lion sat next to me on the bed and proceeded to masturbate me. She brought me to the edge twice. What a treat!

As I was starting to fall asleep I realized that I was no longer just comfortable in my cage. I was horny again. Mrs. Lion awoke the sleeping beast. Of course she knew that. It was her intention. Wednesday morning when I added my daily lion tracker status, I wasn’t sure what horny level to put down. I spent most of Tuesday at level 2: not particularly interested in sex, but then Tuesday night Mrs. Lion recharged my sexual battery. I finally decided it was more correct to show the end-of-day status, so I entered “4”.

Speaking of the LionTracker, Mrs. Lion has faithfully recorded every event in our chastity adventure. We started it only a few days ago, but already it is a helpful recording of what we have done and when we did it. Through it and this blog, you are sharing in every event in our sex lives.

It seems to me that both of us are having a lot more sex than we did before I was locked up. I’m sure that Mrs. Lion has had more orgasms in the last nine months than she did in the last five years. She didn’t agree when I suggested it. I think I need to add this activity to our LionTracker so we can have real data to look at later.

One of the lessons I am learning is that it is up to Mrs. Lion to decide how much sex she wants. It is my pleasure to provide it whenever she lets me. I want her to know that my happiness in chastity isn’t tied to the quantity of orgasms I give her. It’s just a super treat whenever she lets me give her some.