Mail Chastity

Shannon left us an amazing comment recently and asked, what I thought was, a great question! We genuinely love when readers engage and ask thoughtful things like this. 

Shannon asked: “Do the three of you have discussions about John being favored for intercourse over cagedmonkey?”

One of the biggest realities of our dynamic is that it’s fluid. It doesn’t follow a fixed script, and it definitely doesn’t always line up with how these relationships are often portrayed in kink tropes or fantasy scenarios.

There are plenty of times when it might look like John is favored, especially during the lead-up. We’ll tease & edge cagedmonkey for days, sometimes a full week before John even arrives. On the surface, it can feel like John and I are the ones holding the power together, until the moment actually comes, and then… the roles can flip entirely. We don’t have sit down over coffee discussions so much as fantasy chats where we talk about different ideas or things we might want to try and see how they feel. 

Ironically, John often finds himself in the cuckold role… supporting, assisting, and serving while cagedmonkey is the one who gets to feel me and enjoy that sweet release. 😁 Other times, it goes the opposite way where cagedmonkey is the one denied, restrained, teased, or made to watch and want. There isn’t a hierarchy carved in stone, and there’s no scorecard being kept.

That’s the part people sometimes miss: real-life dynamics aren’t clean-cut. They’re responsive. We do what feels right in the moment, based on energy, desire, and connection… not on what we think we’re supposed to do.

And ultimately, it all comes down to Me. They both know that. Who is touched, who watches, who waits, who serves, it happens because that’s what I want, in that moment. That control, that ability to let the dynamic breathe and evolve… that’s the real beauty of being the woman in charge.

Thanks again for reading, and for being curious enough to ask. That’s what keeps these conversations fun and real. 

Look forward to more.

M

Ooo I’m so excited! We got an email recently from one of you lovely keyholders asking some very important questions. I decided to make this another one of the famous “Mail Chastity” posts so that it could be helpful to, not only the person asking, but to the many readers and people out there on the internet looking for the same answers.

So JustUs wrote telling me about how they want to be their best (leading/keyholding) self for their partner which I think is amazing! They feel like it’s becoming a largly chaotic duty without some direction or road map or guidelines to adhere to.

To follow are a bunch of questions I pulled from the email that but the extremely short answer is: it’s your life, do it any damn way you want and no one can tell you which way is the right way – you make the rules! You make this exactly what you want it to be, the way it works for you, your partner and your kinks.

Should we have a Chastity Contract/Agreement?”
We started out with a contract in the beginning… I don’t know that a formal written contract is necessary for everyone but what I do know is important is shared and agreed upon expectations. What I mean is that you as the keyholders and the person wearing the cage have responsibilities and it’s important that everyone understands what is expected of them from the beginning. When we started it we reviewed our contract or our agreed upon responsibilities often (once a month) as things were going well that interval got longer and longer. As we settled into our lifestyle there was really is no need for that since… It’s just life now.

Do we need to have punishments and rewards?
This is 100% up to you. I’m not all about rewards and punishments and stuff like that. I’m simple, follow my rules. You violate the rules, the cage comes off and we are done. I don’t play games, I don’t like bratty bullshit, I don’t find it funny. It’s perfectly fine if people like that and find it cute and want to correct and punish and like that stuff. Please, Don’t get me wrong at all! It’s just not my choice so… The answer is, you choose. Yes, you can make rules and have punishments for when they are broken and rewards for when things are followed or however you want to dole out rewards or you can skip all that. Whatever makes you feel happy and fulfilled as a keyholder.

Are we going to have daily routines or rituals, schedules?
Rituals… That kinda reminds me of pro dommes and not a loving lifestyle marriage but that could totally be an aspect of keyholding that you want and that’s OK, again… This is what you make it. As far as routines, yes, I think routines are probably very good to have in the beginning, until things settle in and become more natural. When we started out we had a notebook and we journaled (feelings, what was working, what wasn’t or things that might be tough to say out loud) often – this was a requirement in our contract, certain phrases being spoken, always doing a certain task… Those specific things can help be a reminder and training tool to help set the lifestyle up for success… On both sides.

I found one woman who had a spreadsheet of all her Caged Cock’s daily tasks.
Personally, that is entirely too much work… Are you looking for a job or to enjoy your man in chastity? I could never do something like this. To me, this is meant to be enjoyable, exciting, arousing… Not work, not daunting, not something I have to sit around constantly coming up with ideas about and thinking about how I’m going to make it work for him… It needs to work for you… It’s not about him. Now if making spreadsheets is a kink of yours then by all means, open excel and go for it. Just remember, this is for your enjoyment, your pleasure, your attention. This is not for you to spend hours coming up with ideas to make it for his pleasure or even displeasure. Work together in the beginning, come back together a few times to find out what is and isn’t working and reconfigure as you need to but ultimately… This is yours to make your own and create something beautiful for you. Make him work to give you the pleasure, the arousal, the excitement.

How will we decide when and for how long he will be in or out of the cage?
You decide – 5 min, 5 hours, 5 days, 5 weeks, 5 months, 5 years! It’s all up to you… No one can tell you the answer to this. Obviously, at first it will come down to wearablility of the cage, how you want to do this, is it a lifestyle? A weekend thing? A bedroom game? Do you want to be in control all the time? Sometimes? Have the key? Give a girlfriend the key? Offloading the decision making can take pressure off but also take away some of your control. Rolling dice to decide a length of time isn’t you deciding but some people have a hard time telling their spouse No, you can’t be unlocked. Or, you have to be locked for a certain amount of time so they let something else decide. Overall, you are still in control because you are deciding what you want to control and what you choose not to… Letting dice or a wheel spin or punishment or reward decide is still controlling and still making your keyholding and chastity journey your own.

**which BTW I don’t think your AI dice game was a waste! I think it’s great to research and find ways like that to help along the way when you might need it! Use it, whenever you feel you want to… No right or wrong – you make the rules!

I’m sure I’m completely overthinking this. I’d love to hear any words of wisdom, advice, relatable experiences, or helpful resources that might help me get out of my head and just enjoy this new adventure.
Yes, lol you’re totally overthinking this… But aren’t we always?? 😂

I hope somewhere in here I was able to help you out and give you some good advice! Check out Episode 3 of our podcast. It’s about praise and reassurance and it’s just me talking to other keyholders and who knows, it might be helpful! Also, the Mistress Ivey books are a great resource… Take what you can use and leave what you will… As much as I love the work she did I disagree with it being presented as the one and only way you should be doing things. There is no should… Only could, because this life is yours and your partners and it needs to be by you, for you.

Good luck to you both and please come check in with us and let us know how things are going and what things are working for you!

Many people are out there wondering – I know, because I’ve received a lot of emails from people like T and David S. asking – exactly how does this whole thing work? How do I deal with and handle the fact that my wife has a boyfriend? And how does this dynamic work into our kink lifestyle?

Well, starting with the “real life” stuff: it wasn’t easy at first. It took a lot of work – a lot of which I’m not sure I (or anybody) is willing to go into yet – but it essentially came down to this: both John and I love M; and if she is meeting both of our needs, is there really a problem? Knowing that Madam truly cares for each of us uniquely (as well as both of us together) is what makes this work.

In practice, that means each an understanding that we are each valuable and needing time and attention. That means date nights for both him and me – it’s a little more difficult for them, with the distance involved, but it’s important to prioritize. It also means taking the time to bond as a group – going out on a date with the 3 of us, spending time together, etc. These things help build trust within our dynamic, as well as a comfort level that is needed in order to enjoy….
Other things.

Speaking of those other things….
One may think that, because my wife now has a boyfriend, that I take the cuckold role; others may think that, because he spends most of his time locked and I don’t, that I would assume that role. In reality, neither is correct – there is an interesting fluidity in the roles we take (other than M being the dominant, of course). Depending on her mood, my wife will have sex with John while I’m only allowed to sit and watch; she may also have me ruin my orgasm inside her pussy so John can clean up the mess that is left behind.

There’s no “set in stone” way we handle things – it is very much “in the moment” and very much “M-driven.” And trust me, she enjoys it this way! She likes the idea of being able to deny both of us… or, for that matter, enjoying us both at the same time!

It wasn’t easy getting here. But the way it works is that we concentrate on each others’ needs, communicate clearly and openly… and most importantly, focus on enjoying the experience (however it may go in the current moment).

A couple weeks ago we posted a blog post about how it’s been 226 days for Cagedmonkey since his last orgasm and a friend, at She rules the Rooster, had some really good questions I figured we should answer in a post as opposed to them getting lost in the comments section. I’m sure other people have had the thought about what I’m getting out of such a long denial period for hubby. I mean, if we were poly or into cuckolding, that answer would be easy but we aren’t so it becomes a bit more complicated in the “what does Lady M get out of it” area.

When it comes down to what I’m doing daily… My sheer extreme sexiness is what teases him, don’t you know?!?! Lmao Seriously though the daily stuff is all about the little things. I’ve pointed out in posts before and even in a podcast if I remember right about the little things. Keeping things talked about, even if it’s in text message or little flirty butt grabs when the kids aren’t around. Making him kneel in front of me while I sit on the couch… It might look innocent enough like daddy is snuggling with mom giving her a hug but to CM and I there is much more behind it.

Making sure that we both know the why’s behind the denial and the lock up are so important. Otherwise, it just becomes an afterthought and can actually become work. So talking about and knowing that I love to see and feel the frustration he is going through makes my pussy wet causes an amazing circle of turning him on which again just turns me on.

At the moment, pleasing me in some fashion is at least three times a week but we say there is so much more to intimacy than actual sex so much more becomes pleasing. CM is pleasing me daily but that wouldn’t look like him eating my pussy or making me come or any of that… It’s more like a back rub or spooning snuggle time or maybe just some boobie play time. Yes most days of the week I am having him give my pussy some mouth attention and maybe some fingering. The day to day stuff though isn’t some long intense teasing session. During the week we are usually tired and in bed early for a 4:30 or 5am wake up. So they are quick “my pussy needs good night kisses” while I run my nails across his back and butt type nights.

There are nights I make him sit or kneel at the side of the bed with his arms clasped behind him. I will take my boobs and smoosh them in his face, make him smell and lick under them so he can’t really get an idea of my day. Then I may run my nipples across his lips, not allowing him to open his mouth. It’s so fun to watch and feel his breathing as he gets so frustrated, desperately wanting to feel it in his mouth and on his tongue. He will even whimper and beg sometimes, “please.” hahaha I love it so much!

I’ll be honest with you… I have in no way been counting how many orgasms I’ve had. I just have them when I have them and when I want them. Most nights our pleasing and teasing is a short thing so I don’t even really want to cum. It’s more work on a woman than you think lol. It takes a lot of thinking and then there’s this whole body muscle tightening thing that goes on. With my chronic pain, orgasms tend to last a few days within my muscles and make things sore so it’s just as good to enjoy the pleasing than to have some intense orgasms all the time. If I were to really think about it is probably been about 1 a week average… So you figure that out… About 300 days divided by 7 lol!

Anyway, thanks for the comment and I do apologize for the delay in getting it posted… It’s sat in my drafts and been worked on as much as I can when I get a moment! I appreciate you reading and being subscribed! If you haven’t checked out She Rules the Rooster, yet, what are you waiting for? It’s always fun to see how other people live their lifestyle… Get on it!

Cagedformymistress asked the following question on Twitter in response to my last post:

How are you even managing to have your cock in her pussy and not cum?

I get asked this a lot, actually. For starters, it’s not easy. Just this morning, ML and I had some “sneak away” sex while the kids were doing their regular morning breakfast/Youtube routine, and her pussy felt soooooo damn good. We haven’t had PIV sex for a couple of days, and she’s usually super tight under those circumstances. Plus, she wanted it from behind – her ass up against my hips, her pussy squeezing my cock nice and tight… damn I wanted to cum so badly.

But yeah, I had to stop. Because it’s still at least another 6 months before I get to cum….

Oh yeah, right! The question of how I don’t cum during sex…. sorry, got a little off track there.

The first thing to know is that I have experience with knowing how far I can push myself before losing it. Even before starting this blog, ML and I had fun with some low-key orgasm denial (she’s always been a cock tease, tbh). Because of this, I know when I need to slow down thrusting (or, in some cases, stop entirely) to avoid cumming. ML knows my tone of voice in these situations, can sense when it’s a true emergency, and allows me to take my time… although, sometimes she forces me to go a little longer and then pull out if she wants me to ruin my orgasm with her pussy (that’s a new favorite torture of hers).

The other thing to consider is that I usually can’t spend a lot of time with my cock as actually inside her pussy – if I did, there would be no chance of avoiding an accident. I almost always need to stop fucking her after a minute or less of actual sex. The short gifs you see on the blog aren’t just a small clip of us fucking, it’s pretty much all I can handle.

So, now you know the secret – I’m able to avoid cumming because I know when to stop, and I know not to push my luck for too long. I’m lucky that ML doesn’t mind that I can only give her sex for a couple of minutes maximum. She actually enjoys the fact that her pussy feels so good that it would make me cum in 20 seconds if I didn’t stop. Besides, if she didn’t want it this way, she wouldn’t keep me in this hyper-horny teased and denied state.

I got a great comment on my last post which included a question I didn’t want to just answer in a reply. I feel like I have a little more to say on the subject than just a few words to be lost in the comment section of the blog.

Philip wrote:

I have a question that I do not recall being discussed in your blog. CM has often edged himself as required but would you Lady M ever instruct him to ruin his own orgasm and do you CM feel you could manage to do this? Personally I think I would find it very difficult and I dare not even hint at the idea to my wife!

It’s interesting to have this question asked because, I do enjoy so very much giving Cagedmonkey a good ruined orgasm. I love, even more, getting him so worked up and crazy during denial that he starts begging for one. I love hearing him moan and whimper and react to teasing and feeling how horny he is. So horny, that he would even want to get that close to orgasm only to have it completely unfulfilled and ruined.

Now to get to the point of answering the question… I do not recall that I have ever had him ruin himself, but himself. I really haven’t even had him stroke or edge himself (without me there) until recently. I struggled a lot with allowing him out of his cage while I wasn’t there. He’s proven, over the past 7 years, that I can trust him to obey me and follow my rules and only do what I tell him to do when he is out of the cage and not with me.

I think one of the other reasons he hasn’t done this on his own is that I enjoy it so incredibly much! Though, he has been the one to actually ruin himself before. I’ve had him both stroke and have sex with me and get himself to a ruined orgasm. A couple of weeks ago I had him fuck my pussy right to the point where he pulled out and his cock just dripped a ruined orgasm on my belly. It was awesome, it makes me so happy I just can’t help but giggle!

Philip, I hope this answers your question and helps you understand my side of this. I don’t know if hubby feels differently when I’m the one ruining him or if he is made to ruin himself. It must take a hell of a lot of self control to do as he is told and to force himself to ruin an orgasm… He could easily just go further and enjoy it but, instead, he obeys because he knows that I enjoy it so much.

So much of his submission is just because he loves making me happy and doing what I want him to makes me happy.

I received a message from another keyholder on chastityforums.com. She is a bit new to all this, in general, and is struggling with how to be a KH and a good one at that. So here is a bit of what she wrote and my response.

My ‘vanilla self’ is constantly fighting with ‘the KH self’ I’m sure [my hubby] would like me to become. I’m not even sure how to make this change. Do you have any ideas to help me in my quest to transition from vanilla to a true KH in every sense of the word?

First of all… This isn’t about you becoming something your hubby wants you to be. This is about you both enjoying this the way YOU enjoy it, whatever way that may be. Please do me a favor and don’t try to be and do things that are not natural. What you do should feel good and exciting to you. If you fake it, it will become work and then you could easily build resentment by trying to live up to his expectations… Do what you enjoy and are comfortable with. You are in charge, you hold the key, literally – he should not be in charge through you when it comes to chastity or keeping him locked etc. That is called “topping from the bottom” and that’s not ok. It is perfectly fine to communicate – if you know me at all I’m huge on communication – so talk and listen to each other. Get to know what you like, what you think you like, what you don’t like, what feels good both physically and mentally. Decide from there what YOU want to implement in your relationship.

Don’t be afraid to try things if they are not a hard No! You may like them or maybe not and you have the choice, as the one in charge, to say yes that’s good we will do that or no that felt bad or uncomfortable and we are not doing that! It’s all good. In the beginning it’s all about talking and trying and figuring out what works and feels good. Don’t be afraid to say no or change your mind either… Try hard to remember, in most situations, he is the one that asked you for this and decided to give you control. He doesn’t want to decide what happens with his sexual desires, his orgasms, his pleasure. He wants you to be in control of it all. 🙂

In regards to how to be a good keyholder, please feel free to listen to Episode 3 of our podcast. It’s about praise and reassurance and it’s just me talking to other keyholders and I think it might be helpful!

Good luck!

We got some awesome feedback today about the podcast and a couple questions, as well, that I figured I’d take a moment to answer. We always appreciate when our readers or listeners give us feedback or just want to write and say, “Hi!” Don’t be shy! 🙂

Love it! The punishment /funishment thing to me is one of countless blurred outlines of that classic BDSM conundrum… if I want to be punished then how can it be a punishment? In my head, it still can be – especially (to your point) if you know your partner and love them enough to exploit that knowledge.

Love getting feedback like this. This is why we love having the conversations we do on our podcast. Having a relationship, kinky, vanilla or whatever really does come down to communication and knowing your partner. Amazing things can happen when you know, just as this gentleman states, how to exploit the knowledge!
I confess that I’ve only listened to a couple podcasts now (just found you guys on Friday), so I apologize if you’ve gone over all of this stuff many times before, but man I have so many questions 😛 Feel free to ignore them…
That’s ok… some times answering things again is a good thing for someone who is new around here. We have answered these before here in the blog and possibly on the podcast but I don’t mind answering them again.
Do you still control / keep other guys in chastity besides caged M? If so, how many? How do you find the time and energy to keep up with that?
I no longer have “subs on the side” and there are two reasons for this. A) I tend to be a bit too intense for most people and they end up not handling being dominated by me very well. The whole fantasy vs reality thing… I make things very real and the intensity of the reality becomes too overwhelming. When I have subs I put my whole self into it and when boys get overwhelmed by me I tend to get myself hurt in the process. And then, B) well like you mentioned, time. I just don’t have it anymore. When I was a stay at home mom I had a lot more time to spend focusing on kinky things. Now I work outside the home, have to take care of my home, kids and they are very active kids and we are involved parents… It leaves very little time for extracurricular activities.
I remember hearing caged M adamantly defining a limit about physically playing with other people, but that you guys might role play with the idea from time to time. How does that generally look for y’all?
There is a really great post here on the blog about Pseudo-cuckolding that you may find helpful in regards to this question. We do not play outside our marriage… At least not with men. We have talked in the past couple years about me having an Alpha sub female to play with but so far we haven’t found anyone that fits.

For me, chastity is inextricably linked with cuckolding, but the reality of that fantasy carries potentially damaging emotional remnants… I’m so curious on how you guys feel about that and if the implication exists in some form within your D/s dynamic.

We have seen how a lot of times people automatically think chastity = cuckolding but we try hard to get across that that’s not necessarily true. That chastity is not specifically one thing or another. It doesn’t have to be this or that. Just because someone is in chastity does not mean the partner goes out fucking other people. Chastity is exactly what the couple wants it to be. It certainly CAN be all those things or none of them. It’s up to the couple to decide what chastity is for them.
Thanks so much for sharing your story so openly and responding : ) I fucking love the internet.
Thank you, so much, for the great feedback and the questions. Hopefully I’ve successfully answered them but please feel free to ask whatever else you want to ask! 🙂 and yeah the internet is pretty awesome!

D & J are a couple that read our blog. They recently sent an email asking for help with appropriate punishment. I’m extremely lucky in having a very good boy who does not push the boundaries so punishment doesn’t not come up often. It’s not something I enjoy having to do.

D & J wrote:

This weekend I have gone away for a few days, on Thursday night my cage worked itself off and I couldn’t get it back on as the key is 2.5 hrs away.
On Thursday night I edged myself once, haven’t done anything else but this is a serious infraction in our relationship.
Previous punishments have been whipping, and a few minutes with clover clamps. Extending chastity has never been a punishment as my wife has never set a time frame to extend until now.
Can you suggest an appropriate punishment please?

My suggestion for punishment may not be like others since I’m not too big into giving them. When it comes to punishment for us I take things away from Cagedmonkey, such as parts of my body, pleasing me or even playing video games. There have been times where I took away chastity and any attention to his penis. Those things really are punishment for him because he enjoys our play and taking that away is really the best way to keep him in line. I don’t really use spanking, etc for punishment as that is more “funishment.”

So the reason for this post is to ask our readers what their suggestions would be in this situation for punishment. What have you or your Mistress done as punishment in this situation? If you haven’t been in this situation, what would you do? What do you feel is an appropriate punishment for edging without permission?

Please comment here in the comment section so D & J can read your responses!! Thanks 🙂

Not too long ago I got asked this question and while I get asked questions frequently, I wanted to put this particular question in its own Mail Chastity post. It’s such a loaded question and it will take much more than a paragraph to answer. As a matter of fact I could do a whole podcast on this question alone. So anyway, here is what I was asked:

Good morning Lady M! …what makes a good submissive. I am curious as to your personal opion.

I have many opinions on what makes a good submissive but the super short, honest answer is – being what your Dominant wants.

That answer is also so incredibly vague! No one, absolutely no one can tell you how to be a good sub. The reason I say that is because every single Dom is their own person and every single sub is their own. They all have wants, needs and desires. The ultimate in being a good Dom or sub is having a Dom or sub that compliments your needs, wants and desires. What it takes to be a good sub is getting to know the person you want to be submissive to. Making sure you know what they want and expect out of a submissive. Once you know that and have learned those boundaries then you know exactly how to be a good sub. It takes work and communication, on both sides, to really understand what the other would consider good.

Let me give you an example of what I mean. I am a very loving, mothering Domme. I am also a very service driven Domme. I enjoy being in control and taking care of people. I like being the one to dictate how Cagedmonkey’s day will be, making his lunch and helping him know what to expect from his day. I also get extremely fulfilled by someone doing things for me, without my asking (most of the time), because they thought of me and wanted to make things easier or less for me. You know those times when CM will be home from work and do dishes or clean and vacuum the living room because he just knows I’m at work too and it will be helpful and make less for me to do when I get home… Those things, in my eyes, make him a good submissive husband. However, that’s only one side of being “good.” I also love that CM is exactly what I need sexually. When I’m feeling hardcore, rough and aggressive, I love that he can take what I am needing to give. When I’m feeling loving and cuddly, I love that he can hold me and love me and be that for me. When I want to be pleased sexually, CM is there to please me how I need it. Whether that’s eating my pussy, making me cum, or just being my sex toy to hump and play with. Those things make him a good sub for me.

What makes him good for me, though, may not be good for someone else. Someone else may want certain rituals daily, tasks that must be completed, hard rules that must be followed or there will be punishment. There are also subs out there that have that need. Strict rules to follow with punishment if they are not. Following those rules and taking that punishment would be what makes them a good submissive.

Basically, what I’m saying is… It takes getting to know someone and communicating to find out what will make you a good sub. I hope, in some way, for some one, this was helpful. There is no one way, no right or wrong way. The whole thing comes down to what works in the relationship and in the dynamic.