Category: Anal penetration and pegging

lion anal discomfort

As Mrs. Lion wrote in her post yesterday, I got Autoblown. This is our latest male sex toy acquisition. It felt a little strange having my favorite sex toy (Mrs. Lion) sitting next to me while this new electric appliance pumped away. We plan to use it a few more times. Like most sex toys, it takes some time and testing before it can do its best work.

Aside from my native curiosity and the fact that I plan to write a comparison of male sex toys, the original motivation for getting it came from the realization that it was taking me a very long time to reach the edge. I reasoned that if Mrs. Lion had the help of a mechanical device it would spare her hands and mouth a lot of extra work. Once the mechanical sex machine got me reasonably close, I figured she could take over. Of course, the first problem is finding a sex machine that can get me reasonably close. I’m not an easy customer.

Autoblow ai. It felt good, but not great.

While I can’t claim that this first Autoblow experience was even close to orgasmic, it kept me hard the entire time we were using it and I had a semi-erection for quite some time after it came off. That’s pretty good considering that I was distracted by the need to wash off the lube.

I’m very sure that I’m over the hump so to speak since during my recent slump I almost never got an erection for nearly 3 weeks. Things are definitely perking up. Unfortunately, my wild days are numbered. The Evotion chastity device will probably get to me within the next couple of weeks. The folks at Evotion have the device ready but need locks for it. I’m very impressed that they use the German-made locks instead of the much cheaper, fairly low quality, Chinese versions. European products are much more secure. It’s fairly easy to pick a Chinese chastity lock. I saw a guy do it in a YouTube video using a foil condom wrapper. That is definitely not the case with the German product.

I’m probably within a week or two of needing waxing again. Mrs. Lion said that she really hates waxing my legs and she may send me to a professional to do that part of my anatomy. Mrs. Lion has become a very proficient waxer. At the same time, the hair grows back sparser and thinner. That also helps speed things up for her. My legs are several treatments behind the rest of me. That hair still grows back fairly thick and heavy. It won’t last under steady waxing.

mrs lion removed all of lion's body hair
Mrs. Lion is okay giving me a Lion-kini and chest waxing, but hates doing my legs.

We will probably resume anal training very soon. As with spanking, each time Mrs. Lion penetrates me she is more confident and less concerned about my verbal feedback. Before anyone gets upset that she doesn’t listen to me, she does but my verbal reactions to what she is doing turn out to be less reliable than what she can feel directly. There’s a certain amount of discomfort involved in anal training. As in all things, Mrs. Lion is the best judge of how much she should push me each time.

This is all within limits that I can handle. If I am really in trouble I can safeword and she will stop at once. There are times, maybe too many when I would rather she stop before she really should. It’s that time after I want her to stop and before it’s really too much for me that represents my best opportunity for growth.

The same is true of spanking. We both share the goal that a spanking should be felt for at least a day after it was administered. A few years ago, Mrs. Lion tried starting out with very hard swats. She couldn’t get past seven or eight before I rolled away. Two things were going on: The first was that I was unable to develop a tolerance for the sensation. The second was that I didn’t have enough experience to understand fully what I was feeling.

Over time, she learned that she needed to build up the force more gradually. When she did that, I was better able to manage the sensation. It did mean that at the beginning of spanking, it didn’t hurt very much. It turned out that was a great benefit. During that relatively painless time, I was able to adjust mentally and physically. When she stepped up the speed and intensity, the pain grew but not so much that I couldn’t hold still. Over time, she was able to do more and more as I learned to manage the sensations. Now, she has no trouble making me feel a spanking for a day or two after she’s finished. I also can tolerate it, but hate every minute. Job well done.

Anal training isn’t too different. The objective isn’t necessarily to cause me pain. It’s to teach me to relax enough to accept whatever she wishes to insert, even her entire hand. Just as with being trained to take a spanking, I have to learn to convert the unpleasant sensations into relaxing my sphincter muscles to allow her to complete penetration. Eventually, she will be able to do that.

I knew someone years ago who fisted all of the men she dated. She told me that with patience she could generally get the job done in the first session in less than an hour. I told her that I was pretty sure it would take more than that for me. We never got to try.

One of the things I like best about our power exchange is that I have to grow to meet Mrs. Lion’s requirements. I know that she doesn’t really want to hurt me, but she understands my need to accept her in every way possible. We both learned that spanking has moved from being a BDSM activity I’ve always enjoyed to becoming an excellent way to train me. Now that she has learned that things can only get better when she does this, she is far more willing to advance my education.

A Simple Technique For Easy Anal Fisting

I realize that based on the title of our blog, we should be writing mostly about enforced male chastity. Well, after nearly 4,000 posts, one would assume that we’ve said pretty much all we can on the subject. That’s not entirely true. We keep learning new things and trying new devices. However, our most recent activity has centered on the flip side of my body: my butt.

Mrs. Lion and I have done anal play for at least a decade longer than we pursued enforced male chastity. She has strapped me into our sling and progressively peg me with larger (thicker) dildos over the years. It’s always been uncomfortable and I’ve never been able to tolerate much in and out movement. That kind of activity dropped off some time ago. However, Mrs. Lion has always enjoyed inserting a butt plug and letting it marinate for a few hours.

Anal play has never turned me on directly. That is, I don’t get hard when things are shoved up my ass. But I do seem to get residual arousal once the activities are done. There’s a pretty good reason for this. For one thing, inserting things and moving them massages my prostate. This is absolutely beneficial to any man. It provides a kind of indirect sexual arousal as well as promoting the health of that gland. Of course the prostate can be massaged with a single finger inserted about 2 inches into the anus. Mrs. Lion’s method is more fun.

Anyway, all these years I’ve been going about this the wrong way. I am the principal source of knowledge on topics of the sword for Mrs. Lion. I’m the one that suggested that I could be trained by having her insert and move larger dildos in and out of my butt. To some extent it worked. She always expressed an interest in being able to get her entire hand inside me. All those years all I could do was uncomfortably accept two, occasionally three fingers. She gave up after repeatedly getting stuck at this point.

Within the past few weeks I did some casual research into fisting. I had seen a video of my wife fisting her husband. I got a little excited when I looked at it and wondered why I couldn’t get fisted by Mrs. Lion. So I decided to do some research. I went to my favorite librarian, Google, which offered me quite a few opportunities to learn more. Unsurprisingly, most of the references where useless. However, I came across a few articles that seemed authoritative. Interestingly, they all agreed on technique.

Their first point was that nobody just bends a guy over and rams her hand up his ass. Porno’s that show fisting have “rehearsal” where the man is prepared for the final shoot. I never considered that. Anyway, it turns out that my idea of using progressively thicker dildos isn’t particularly useful to train for fisting, or for any other anal activities. The problem with it is obvious. Inserting a dildos involves essentially forcing a cylindrical object past the anal sphincters. Once they are opened by this object, they remain open. If the object remains in there a while, they will grow tired and involuntarily relax a bit. This is what made pegging begin to get comfortable for me.

full hand inserted in anus

Mrs. Lion is very close to achieving this. Our new training technique really makes this possible for the first time.

I did learn to relax a bit so that subsequent sessions were little easier. But the fact is that my body wasn’t really learning anything important. It turns out that the key to comfortable anal activity is learning to relax voluntarily. This isn’t as easy as it seems. The sphincters are muscles that are normally contracted. That’s a good thing since it holds the poop in. Pegging, fisting, and other anal activities require that the sphincters relax to give admission to whatever objects are being inserted.

It turns out that it’s fairly easy to learn to do this. Instead of using dildos, anal training should use butt plugs. The reason for this is that butt plugs are triangular-shaped. They start with a blunt point and steadily expand to their full diameter, then there is a shoulder which suddenly reduces the diameter substantially. When one is inserted, the anus must slowly distend to accept the increasing diameter of the plug, then suddenly shut down when the shoulder passes it. The reverse when it’s removed is that it has to expand for diameter, then slowly shrink back as the plug is removed.

I always found inserting and removing butt plugs very uncomfortable. Once they were nestled safely inside me, it felt good. Okay, training isn’t about that good feeling. Instead of just inserting the plug and letting it marinate, it’s inserted and then removed immediately. It’s reinserted and removed again. Essentially I’m getting pegged by a butt plug. Mrs. Lion started with a small size (Thank goodness!) And gradually moved to larger and larger sizes.

The first time and went in I was as uncomfortable as ever. When it came out, ditto. The next time, which occurred only a few seconds later, was much easier. It didn’t take very long before there was no discomfort at all. The reason for this is that the plugs taught me to voluntarily relax the sphincter so that the plug could move in and out without hurting me. Aha! I was learning to be in direct control. Well, not entirely. I can’t open my butt on command. But, it knows what to do when something comes knocking.

It didn’t take very long at all; just a couple of days until I was easily managing our largest plug. A good part of our success had to do with the lube we used. Some of the articles I read about fisting talked about appropriate lubrication. It turns out that there are a few products that work very well in the anal arena. The two top rated ones are powders get mixed with water to produce a slurry of the thickness the Pfister would like to use. The third is a premade cream. I selected that one and ordered a jar. It’s called Eros. It’s a very special formula and very expensive, by the way. In any case, it works wonderfully. Both Mrs. Lion and I think that this loop had a lot to do with her success.

Anyway, on Friday I asked Mrs. Lion if she would like to try fingers again. She agreed and that evening instead of plugs, she used her fingers. Unlike my previous experiences, it didn’t hurt at all. It was a little uncomfortable at first, but then just a mild stretching sensation. I kind of liked it. When Mrs. Lion was done, I asked her how many fingers she got inside me. Initially she said three. Then she corrected herself and said, “Four.”

Wow! We never got near that before. Four fingers! Holy crap! I took them comfortably. When we talked about it we expressed how surprised we were at this success. Adding the thumb isn’t going to be immediately easy, but we both agreed it’s very likely she would be able to get her entire hand in within a reasonably short time.

We watched a couple of fisting videos to get some idea how other people do it. Then we settled in for a relaxing evening. I had absolutely no ill effects. I think if we keep this up on a daily basis Mrs. Lion will soon have success. She used to go in “bareback” with no rubber gloves. On Friday night she had on a glove. I asked why and she said that I had once told her that it was much smoother if she had a glove on. This is true to some extent. The glove protects me from any sharp nails or other potentially scratchy things. However, if she’s careful about her nails there’s no reason she can’t go in bare-handed if she wants.

She mentioned that it would be nice if they made longer rubber gloves. The ones we have just go to the wrist. This isn’t enough if she is going to get her entire hand inside me. I suggested she do a search for long gloves. She did and found 12 inch and 18 inch long gloves on Amazon. I ordered a box of 12 inch. This should be perfect for when she wants to go in gloved.

Since we had spent well over a decade attempting to teach me to accept her hand and had nothing even approaching success, this past week has been nothing short of a revelation. With the use of just a few inexpensive butt plugs and a jar of expensive lube, Mrs. Lion has been able to train me to accept four fingers. I expect that she will be reporting success and fisting me by this time next week.

I guess this goes to show that you really can teach an old lion new tricks.

anal trainer kit

I’ll start with the smallest one. Lion thinks it’s too small for him, but he’s never been pegged by a butt plug before. He may be surprised how hard that little thing is to take.

We decided to go to Ikea yesterday. Lion needs better storage for his office space at home so we’re moving things around. Needless to say, I didn’t really get anything done around the house. I’m hoping that will happen today. Although, the things I’ll get done are most likely not much unpacking. However, getting Lion’s office space figured out goes a long way toward making the house more livable.

It was about 8:30 when I shoved the butt plug up Lion’s ass. We didn’t get the early start we hoped for. It must not have been too uncomfortable because he snoozed while it was in. When I tried to wake him up, he said he was ready to play and then he was out again. We finally wound up playing around 9:30 when I removed the butt plug. I’d guess we were at it for about a half hour. I don’t think Lion ever reached a full erection but he was bucking away. I know it felt good for him even if nothing was really happening.

After our attempt at fun, I told Lion he forgot punishment day. I said he owes me a diaper day. Then I suggested that we no longer really need punishment days. I punish him on the day of the infraction, assuming I remember. This, of course, would eliminate a source of infractions. And, Saturdays especially, is a good source of infractions. We decided recently that rules like these are misdemeanors so he wouldn’t be avoiding serious punishment, but perhaps I’m being too hasty in cancelling punishment days. Any opportunity for punishment of any sort is welcome. For now, we’ll keep them.

We got the set of three butt plugs Lion ordered so we can begin anal training. At first glance, they look laughably small. He said the smallest one is probably not usable. However, if you consider that these will be going in and out like a dildo, the smaller one might not feel all that insignificant. I think we’ll start off with it. If it is too small we can certainly move on to the next size. We’ve never used a butt plug like a dildo before so I’m reluctant to start out too large. He’ll need time to adjust.

As I mentioned, Lion is in a diaper today. I allowed him to pee before putting on the first one. From then on he’ll have to pee and sit in a wet diaper. He can change from that wet diaper just before he has to pee again. That way he’ll always be in a wet diaper. You’re welcome, my pet. [Lion — Humph!]

anal trainer kit

Inexpensive anal trainer kit. The rings on the ends of the plugs makes it easy to move them in and out. Click image to go to shopping site.

For a long time I’ve enjoyed – well that’s not exactly the right word – anal play. I guess that in my case, stimulating my anus is a little erotic in terms of sexually stimulating me, and very erotic in the mental BDSM sense. Anyway, Mrs. Lion occasionally will do some anal play. In the past, she expressed interest in being able to fist me. That is, getting her whole hand up my ass. All of her attempts failed after the first three fingers. I just couldn’t handle the pain when she tried to get more penetration.

I thought the problem was my inability to relax enough to accept more of her hand. That turned out to be a correct assumption. To solve this problem, I suggested she begin to train me to accept increasingly larger dildos. By larger I mean thicker. Almost all of our dildos are about 8 inches of insertable length. That’s a good size and safe to use. Over time, she was able to get me to accept, without too much discomfort, a 2 inch diameter dildo. This should be wide enough to be about the same size as four of her fingers. Yet I still had extremely serious pain each time she tried.

One school of thought is that I should learn to accept the pain and let her keep going. I don’t disagree. However, this sort of anal training requires a lot of patience on both of our parts. It’s absolutely possible for her to get her entire hand in. However, it takes considerable preparation to get in there. When you see porn videos that show a man being fisted, insertion generally takes a couple of minutes at most. What you don’t see is the long preparation done before the video was shot.

The anus has considerable ability to expand. It’s a muscle that normally stays contracted. Training for penetration has nothing to do with stretching anything. It’s training to learn to relax the anal sphincters; there are two: the one we all see and on further inside. This takes time and patience. Over the years I’ve done quite a bit of research on the subject and only recently did I learn a surprisingly easy and reliable way to get trained sufficiently to be fisted. This training doesn’t use dildos at all.

According to people who have a lot of experience with this, a very good way to be trained to relax when needed is using butt plugs in a different way. Mrs. Lion likes to use butt plugs with me. They are very easy for her. She lubes up the plug puts a little more lube around the rim of my anus and inserts the plug. Then she can go do other things while the plug marinates inside me. The plugs construction is designed to let me retain it without any external devices to hold in. It has a conical shape ending in a shoulder which is a sharp right angle, followed by a stem much thinner than the widest part of the plug, and then at the end a wide base to prevent the plug from slipping inside.

Plugs come in a wide variety of sizes starting from relatively thin ones (about 1 inch in diameter) up to giants that measure four or more inches in diameter. The way Mrs. Lion uses butt plugs is a good way to express her dominance. She generally has me retain the plug for two hours or more. As time goes by, it becomes less and less comfortable. When I’m wiggling on the bed looking for a comfortable position, she usually removes the plug. This is a fine and fun form of anal play.

fisting hand position

Training for activities like fisting and pegging require a different sort of training. In this case, the plug is used very much like a dildo. It is inserted all the way and then removed. Inserted again and again. This is very uncomfortable, at least in the beginning but it’s absolutely critical in terms of anal training. Rather than just training the anus to comfortably accept larger and larger objects, butt plug training teaches the anus to relax immediately upon the presence of something trying to enter.

This makes sense to me. The most uncomfortable part of anal play for me is the initial insertion. That initial pressure and expansion is always the most painful part. Once an object is in and if it’s left there, after a relatively short time it’s easy to retain. The uncomfortable part is the opening and closing of my sphincters. If you’ve done anal play, I’m sure you’ve noticed how removing a butt plug is very uncomfortable as the shoulder is puledl out and then almost immediately feels good as the rest of the plug slides out. Slow pegging with a butt plug forces experiencing that discomfort over and over. After time, I’m told that the discomfort becomes less and less. Your body learns to relax as soon as something is pressed against your anus.

Training this way is done very much the same as with dildos. Start with a relatively small diameter butt plug, and as discomfort is reduced, go one size up. If this is done on a regular basis, say three times a week, over time, your anus will be trained to relax and accept larger and larger objects. This doesn’t take a very long time I’m told. If the sessions are long enough, reasonably comfortable pegging with a plug can be achieved with only two sessions before a larger size will be needed.

Keep it slippery
Let’s talk about lube. Obviously, lots of lubrication is needed to avoid injury and massive pain. Over the years, we’ve tried lots and lots of lubes. The most slippery lubes tend to be silicone. However, since almost all toys are now made of silicone, this lube can’t be used with toys of the same material. It will soften and dissolve the toy. We’ve been using Boy Butter, a reasonably inexpensive lube designed explicitly for anal play. It’s easy to clean up and won’t break the bank if you use a lot.

Eros is a fairly new product that is highly recommended in the articles I read about fisting. It is a silicone hybrid. People say it is safe to use with silicone toys. Experienced fisting advocates rate this particular lube very highly. It is thick and long-lasting. It contains a slight amount of anesthetic that helps make it easier to accept objects. It is supposed to be extremely slippery. I have a jar (it’s expensive, by the way) and I hope Mrs. Lion will use it on her next anal session with me.

For me, anal training is something I love to hate. It’s uncomfortable and the furthest thing I can think of from activities that will make me hard. However, it’s also one of the most visceral ways to sexually submit. Thinking about being fisted is very exciting to me. I’m even excited about being trained. However, I’m sure I will be unhappy during the process.

Some women find anally penetrating their partners very sexy. I know one woman who makes this the first thing she does with any man. She keeps several pairs of rubber gloves in her purse for this purpose. She enjoys taking 45 minutes to an hour to train the man to take her hand. She’s always successful. Unfortunately, the one time she was able to try this with me, we were interrupted just as she put on her glove and began using one finger inside me, she had to leave.

Years ago I knew a couple who love anal fisting. They would do workshops on how to do it at national events. I attended more than one. Her husband was so well-trained that she could make the appropriate hand shape for insertion, lube her hand, and in seconds be halfway up to her elbow. This is probably the most extreme case I know. She really loved doing that to him and he loved it too. I don’t expect Mrs. Lion to be that enthusiastic. However, in the past, she has worked up some excitement about training me.

The subject of “training” really turns me on. In a way, it’s like being hypnotized. I somehow learn to do something without any conscious thought. I call it training, others consider it conditioning. In either case, it’s a very visceral experience to find yourself unconsciously conforming to rules imposed by others. Anal training is a very strong example of this sort of conditioning. To a small degree I’m already conditioned to accept some of the smaller objects we have. It’s easy for me to accept the Njoy metal butt plug. Mrs. Lion inserted it a few weeks ago and was quite surprised at how easily I took it. Maybe that plug is a good starting point for me. Repeated insertion and removal of that plug will be less alien to me. I’m pretty sure it won’t be much fun in the beginning. I’m also sure it won’t take long before it’s easy for me to manage it. Then Mrs. Lion can move on to the next larger object.

Like everything else we do, I guess we have to agree to try and then use a structured schedule to assure we actually follow through. Maybe this could be part of the recreational activity on punishment day. That would be Monday, Thursday, and Saturday. What do you think Mrs. Lion?

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