I poked around last night and couldn’t find our supply of coconut oil. I know we have it. I just don’t know where it is. I guess that means I’m back to unpacking.

Just to prove I don’t know what I’m doing, I was sure Lion wasn’t getting anywhere when I was milking him. He didn’t seem to be getting any harder. He wasn’t making any noises. The only thing that seemed to be happening was that I was getting a little achy. Normally I can deal with achy if I think I’m having an impact on things. I’m not sure how long I tried but I finally told Lion we were done.

Before he got comfortable on his back, I told him to lay across the bed so I could give him some oral attention. Again, he didn’t seem like he was getting anywhere. He did get a little hard but he was still fairly soft when I asked my weenie why he was ignoring me. Lion said he thought he was getting somewhere. It felt good. That’s all I need to hear. If it feels good, I’ll keep chugging along.

I was doing some of my best stuff. Tongue movements, varying the speed, more pressure, less pressure, etc. and Lion was still semi-soft. But then, he was making his I’m-near-the-edge noises. I kept going and I got some cream filling. I’m sure he probably could have produced more semen if I’d edged him a few times, but I’m happy with what I got. It was the whipped cream on my happy birthday.

I do wonder, however, what was up with the lack of weenie hardness. It wasn’t that it took a long time to rev him up. I think the milking did its fair share of getting him excited. The fact that he said he was getting somewhere when I didn’t think he was is strange too. To be clear, this isn’t the difference between hard and super hard. This was more like the times we give up because he’s stalled out.

I don’t think Lion is broken. He did get to an orgasm, after all. And I’ll be sure to keep an eye on my weenie to see if this trend continues. Plus, it’s fun to keep an eye on my weenie.

Even though I had to fix more complex math problems again yesterday, I was in a vastly better mood when I got home. I’ve been more tired the past few days but that didn’t stop me from milking Lion. He says he likes milking because he feels like he’s doing something other than just lying on his back. He gets participation points.

He was surprised when I told him the other night that he humps a little while I’m milking him. He didn’t understand how because he can’t really use his hips. I couldn’t really explain it to him at the time, but last night I watched it more carefully. He actually does two motions. He rocks back and forth like I did when he entered me from behind. And he arches his back which does move his hips a little bit. It may not be as dramatic as when he’s on the bed moving up and down, but it’s there.

I was able to milk him for a little more than ten minutes last night. I glanced at the clock when we started because I was curious to see how long it lasted. Given the sounds he was making, I think it’s possible to edge him in this position. I’ll have to work on my stamina and maybe use some accouterments but we might get there.

lion's penis teased by magic wand
This never fails to get lion hot. He stands up straight for the Magic Wand.

Once Lion was on his back again, I used the Magic Wand. He said he thought I’d use it for milking but I want to see how things go naturally first. Now that it’s clear he’s enjoying himself, I’ll use the Magic Wand. The issue we’re having is that Lion doesn’t maintain his erection for long after we stop milking. The Magic Wand failed us but when I went to lick some precum off he reacted so strongly that I decided to continue on with my mouth. However, that didn’t last long either. We both enjoyed it but he never got near the edge.

Of course, Lion says he’s broken. It’s been a few days of not maintaining his erection. He’s sure he’s broken. He’ll never have another orgasm again. Does this sound familiar? He’s always convinced he’s broken. I’m not. I consider it a challenge to get him to the edge again. I will not rest until he’s had another orgasm! Okay. I’ll rest but you know what I mean. I’m not giving up and he shouldn’t either. He just needs to enjoy all the contortions and acrobatics I go through to get him excited. Just kneel there or lay there and enjoy yourself, Lion. Don’t focus on being broken. Focus on me trying to get you off.

If you’ve been following along, you know that Mrs. Lion has been trying to milk me. To be clear, by “milking” I am referring to me being on my hands and knees, Mrs. Lion behind me pulling my penis between my legs and masturbating me. I am not referring to the so-called prostate milking. For the record, there is a lot of mythology about prostate milking. It’s a process of reaching into the anus and massaging the prostate gland. According to mythology, this will cause semen to come out of the penis without any sexual pleasure for the male.

I’ve had my prostate milked by a urologist. All that comes out of the penis is a small amount of clear fluid. Mrs. Lion has attempted to milk my prostate as well. She didn’t have as much luck as a urologist. I’ve done some careful checking and I can say authoritatively hat semen does not come out just by massaging the prostate. Some guys do produce semen because they have a sort of ruined orgasm brought on by the excitement of the procedure and the prostate massage.

lion's milking position

On Tuesday night Mrs. Lion asked me to get into the milking position. I got on my hands and knees with my legs wide apart. My head was down touching the bed and my butt sticking straight up in the air. This time, Mrs. Lion tied up my balls with a piece of her CBT rope. She used the rope to pull my balls up and away from my penis. This gave her a clear shot for milking.

Like before, she pulled my penis straight back between my legs and began massaging it. It was very exciting. She said I was extremely hard. She milked me for about 10 minutes. She changed positions several times to find one that was comfortable for her. When she stopped, I was nowhere near the edge of orgasm. I had a very good time and my penis was sticking straight down.

She told me to roll over and I rolled onto my back. She sat across from my penis and continued masturbating me. This went on for quite a while. Sadly, I could feel myself losing interest after a while. She noticed too and asked if I was finished. I agreed that I was. I commented that it looked like milking wasn’t working out so well. To my surprise, she said that she thought it might work after all. She wasn’t ready to quit.

If nothing else my position on my knees with my butt up in the air offers her extremely easy access to all of my sensitive spots. It certainly gives her the opportunity to add some toys to the mix. Butt plugs, clothespins, and other CBT toys come to mind. I found I was able to comfortably maintain that position for at least 10 minutes. She was concerned that my shoulders would begin to hurt too much and I would have to get up. So far so good.

Mrs. Lion also told me that I was trying to hump while she was milking me. I didn’t realize that. I couldn’t be very successful since in that position I have very little range of hip motion available to me. There are other positions she could have me in for humping practice.

Getting me off my back offers up a lot of new possibilities. I’m a little surprised we didn’t think of this before. Mrs. Lion and I will keep you posted as our adventures continue.

Monday night Mrs. Lion milked me for the first time. It was, to say the least, an interesting experience. I was on my hands and knees on the bed and Mrs. Lion either stood behind me or sat next to me. She pulled my penis back between my legs and milked me. It did feel different in a very nice way. I couldn’t really tell that my penis was out behind me. All I could feel was her regular motion getting me more and more excited.

This went on for quite a while until my shoulders got too tired to hold me up. Then we stopped. I turned on my back and Mrs. Lion continued in the standard handjob position. I never really got to the edge but I was very excited. Mrs. Lion said that my balls got in her way while she milked me. When my cock is pulled straight back between my legs, my balls ride on top of it. In an email Tuesday morning, she said she wanted to try again and this time would “wrangle” my balls. I take it to mean that she will tie them and then move them out of the way, perhaps by tying them around my neck or to my leg. One way or another she will secure them out of her way.

My milking position

This is the first time in years that I’ve been stimulated when not lying on my back. It felt very good. I discovered that I couldn’t “help” her from that position. With my knees spread apart and my weight distributed between them and my arms, humping isn’t possible for me. I suppose that’s just as well since I’m certainly not supposed to milk myself.

It turns out that that position exposes my ass completely. My cheeks are apart thanks to my spread knees and Mrs. Lion has full access. She took advantage of this position and tickled me where the sun don’t shine. I expect she may choose to do other stimulating things while it is so easily accessible to her. It turns out that the milking position is very good for exposing all my otherwise-less-accessible areas. This might even be a good position when she decides to return to spanking me between my cheeks.

Mrs. Lion never says very much when it comes to sexual activity. I think it might be more fun if she offers some instruction. For example, she might want to tell me, “get in the milking position.”

Then I could make the necessary adjustments and be ready for her on my hands and knees. Similarly, at other times it would be helpful if you would tell me when she expects me to hump her hand. I think it’s exciting to be given directions by her and helps me avoid confusion. I’m sure she can think of other things that she can tell me to do when needed. When she wants to spank me, she will often say, “I want your backside up.”

I then lie across the bed in my spanking position.

She and I are creatures of habit. We have to work to make things different. I think my visits to the dairy represent a great opportunity for me. Perhaps I will learn that I can ejaculate in positions other than on my back. That is, of course, if Mrs. Lion wants that to change. She may want me to only come on my back with my legs apart. That’s fine with me.

We’ll see.