mail chastity

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Mail Chastity: The Keys to Keyholding

Posted by Michele on December 29, 2025
Posted in: KeyHolder, Mail Chastity, Male Chastity. Tagged: , . 2 comments

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!

Mail Chastity: Ruined Orgasm

Posted by Michele on March 30, 2020
Posted in: Mail Chastity, Male Chastity. Tagged: , , . 8 comments

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.

Mail Chastity: Punishment

Posted by Michele on June 3, 2018
Posted in: Advice, Mail Chastity. Tagged: , , , , . 3 comments

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 🙂

Mail Chastity: Guilt

Posted by Michele on April 6, 2017
Posted in: KeyHolder, Mail Chastity, Male Chastity. Tagged: , , , , , , , , , , . 2 comments

I was asked this really great question recently so I thought I would take a minute to write here about it. I’m sure some of our readers who are in control would appreciate it. Then again, some of you in the submissive role may like to know this stuff too. 

“…doesn’t it make you feel bad sometimes when you deny your hubby for so so long? Do you ever feel guilty?”

There actually was a time, when we first started this whole chastity and longer term denial thing, that I would describe my feelings as guilt. Now that we are almost 4 years into this there are zero feelings of guilt. There doesn’t need to be any. 4 years ago my hubby asked me to take control of his sexual pleasure. He wanted me to be the one to decide if, when and how he would orgasm. I gladly accepted that role and took control over that pleasure for him. So why would I feel guilty about giving him something he wanted in the first place? That’s something us dominant types can forget sometimes… but when someone completely offers themselves to us we need to not feel guilty about accepting the responsibility.

Cagedmonkey naturally craves and needs to be controlled and I naturally crave and need to be in control. It makes us both feel fulfilled and content in our relationship and in our life. It fits us so well to accept these roles. 

So, in short, no I don’t feel bad or guilty about denying him orgasm or even keeping him locked in that steel cage and even controlling him to the point of when he gets a full erection. I love knowing that he is THAT controlled, down to something even HE can’t control! I love knowing he has a pretty constant reminder of me and the fact that I control him and he sexual organs and pleasure. It’s mine to enjoy, he gave me that. He offered me that gift and it’s one of the best things and shows such deep love and respect and, more importantly, trust. It makes me feel great, not guilty! 

Mail Chastity: How Do I Satisfy My Mistress?

Posted by Michele on July 7, 2015
Posted in: Advice, Mail Chastity. Tagged: , , , , , . Leave a Comment

We got some more email questions and I thought I would answer some of them here in case anyone else had any advice for our readers.

subhubphx writes:

I just recently posted on my blog about sometimes not being able to fully satisfy Mistress K. when she needs or wants to be fucked really good, really hard and for a long time.  Being her dutiful, chaste, submissive husband, my urge to cum happens waaaay sooner than Mistress needs for her to get what she needs often enough.  I was hoping to get your advice on how you might handle a similar situation that possibly exists with your sub/slave men.

I appreciate you writing for my advice subhub. It’s actually pretty simple, there really is no way cagedmonkey can give me a good, hard, thorough pounding when denied his own orgasm – which I sometimes crave and need – though, he’s gotten very good with hands, mouth and toys. He’s learned to satisfy me through other methods. However, there are times I need it and that’s where a good strap on and “Adam” come in handy.

It’s very hard for me to enjoy insertables because they are usually cold, hard and not all that forgiving and just don’t follow the contours of a vagina. That was until I found Adam (you should be able to use the search function to find posts re: Adam), which is the most realistic dildo I’ve seen and felt and it’s really just a great toy. It’s soft but firm (but still bends a bit with tightness so you do have to help it get going) and feels really great. It warms up quickly and even more quickly when you warm it before under some hot water.

We’ve just found that the strap on harness is the best way to get that “between the legs, hip thrusting, manly fucking” feeling that us ladies do actually crave sometimes. While cagedmonkey is able to hold off longer the more he practices, he’s still not able to pound the hell out of me when I really need it without the strap on.

I hope this helps answer your question and please write us if you have more! 🙂

Mail Chastity: My Wife Isn’t Into BDSM

Posted by Michele on June 25, 2015
Posted in: Mail Chastity. Tagged: , , , , . 5 comments

We got an email the other day and I’ve been going over and over it in my head and chatting with cagedmonkey about how to respond… Honestly, I don’t know! So I wanted to post it here and give all of our amazing readers a chance to share their opinions and offer their advice. I know this subject often comes up on the Chastity Forums and there are many different stories told and suggestions offered. Please take a moment and comment if you have something to add. 🙂

Frank wrote and asked:

I have been reading your blog for about a year and have really enjoyed it. I’m a fifty something who wishes he’d learned about chastity 30 years ago. Survivor of prostate cancer who had a radical prostectomy and now can not get an erection. Sex life is almost non-existent. Married for 37 years but wife not into BDSM. She is very vanilla. Might get her to tie me up once a year. Any suggestions?

Thanks, Frank, for being a loyal reader! I appreciate your email and I wanted to respond here. This is a pretty common subject. Since I really do not have any magic words or advice as to how to get someone’s partner into BDSM or chastity… I will just tell you that the things that helped me the most were honesty, communication (the why is big for me), non-judgemental listening and most of all… Time!

For me I freaked out at first – which I know there is a post around here about it somewhere – but after months of my own reading and research and lots of communication, without feeling pressured, I was able to see that the chastity part of it all had nothing to do with hubby not wanting me or not wanting sex with me but everything to do with control and tons more sex and sexual energy between us!

So there is my “advice” if you want to call it that. I do hope that some of our readers will share their story about how they got started or brought up the subject with their partners.

I wish you luck and encourage you to continue to be open and honest with your wife.

Mail Chastity – Wanting to Learn About Male Chastity

Posted by Michele on February 11, 2015
Posted in: Mail Chastity, Male Chastity. Tagged: , , , , , . Leave a Comment

The other day we were contacted by a gentleman very interested in male chastity. He had lots of great questions and I thought I would take some of them and answer them here! I know he has plenty more and perhaps there will be more Mail Chastity soon with those. Feel free to send us any questions you may have about chastity in general or about us personally. We do love sharing with you all.

BatBoy5 asks:

Do you have a preferred device?

Lady M: As a matter of fact, yes I do. My preference for everyday and long term use is our custom Mature Metal Jail Bird device. If I want to change things up short term we have the Steelworxx Revenge which is a more enclosed steel device. This creates a different sensation for cagedmonkey because it takes away his ability to see his penis as well as some of the feeling that he is able to have in the more open Jail Bird.

Plastic, metal, or silicone?

Lady M: At first I never thought I would like steel so we went with a silicone device CB style device. I never did get to plastic because it just seemed like it would be uncomfortable for cagedmonkey. After seeing what happened with the silicone device it just seemed like a plastic device would break at the pressure of his erection. So as I said we got the silicone and it didn’t even kind of fit. lol Hubby was way too big to fit in those types of devices. He was simply too long and too big around, even, flaccid, to squeeze in. So we ultimately went to steel and I’ll never go back, it’s beautiful, sexy, sleek and much better for the way we do chastity.

Do you build up from short term to long term to “permanent”?

Lady M: I think what you’re asking is did we jump right in to wearing the device all day, every day, right? And, that’s not really possible. You have to start slower with a device, check the fit, make sure there are no issues, and your body needs to get used to having something locked on it lol. There is a learning curve and it does take some building up in the beginning. For us, it only took a few days before hubby was wearing it for hours and full days.

Is there any such thing as permanent chastity?

Lady M: Sure there is, with the right device, fitted properly, a guy could wear one permanently and never have sex or orgasm again. 🙂

Do You find that chastity leads to other areas where you assume control of a boy’s life?

Lady M: I don’t think it has to at all. It certainly can and for us, our FLR/WLM (Female led relationship/Wife Led Marriage) is actually what led to chastity in a way. I’m already in control of everything and hubby asked me to be in control of his sexual pleasure as well. It just worked that way for us.

Do You ever use chastity devices that incorporate piercings or urethral inserts?

Lady M: We do not, I’m not into genital piercings on my own boy (they are very sexy on other people!) or urethral inserts (hubby’s anatomy won’t work with those anyway). I do know plenty of others who do use those types of devices and do actually enjoy Sounding. One of my other boys is actually into that and will play with it on his own.

I hope this helps answer your questions, thank you again for writing and asking. I look forward to hearing from anyone who has any questions. If you’d like to ask cagedmonkey anything in particular just let us know!

Mail Chastity: Questions From a Potential Keyholder

Posted by JonMustWait on January 2, 2015
Posted in: Advice, Mail Chastity, Male Chastity, Wife Led Marriage. Tagged: , , , , . Leave a Comment

A friend of My Lady – who doesn’t happen to know about this blog – was chatting with her about male chastity. How the subject came up without mention of the blog is a mystery, but she asked her a few questions that I thought it might be helpful to answer here. And if ML’s friend happens upon this blog, thanks for the post material!

ML’s friend wants to introduce male chastity into her marriage. She wanted to have an idea of what to expect from certain aspects of chastity. She writes:

Going months without an orgasm – is that healthy?

First, I’m going to be a stickler for terms. There is absolutely no danger for a male to go any amount of time without an orgasm. Ejaculation is a different story: there is some evidence that frequent ejaculation decreases the probability of prostate illness, however there is also evidence that regular ejaculations increase prostate disease. When it comes down to it, nobody really knows. If you are interested in the “better safe than sorry” approach, there are ways to have a male ejaculate without a full orgasm (milking, ruined orgasms, etc.).

What effect does that have on him?

Long story short, it makes him fucking horny as hell. The male body craves orgasm constantly – it goes back to the primal urge to reproduce. The longer he goes without an orgasm, the more he’ll need it. Over time, he will recognize his keyholder (that would be you) as the source of his pleasure, and he will develop a submissive instinct and try to keep you pleased as a result of this. Some people have said that the increase in intensity of this reaction tapers off after a few months. I call BS on that. 🙂 Thanks to ML’s constant teasing, I’m still feeling that need to cum grow and grow every day.

How does a keyholder stay stasified without sex?

There are ways for a man to satisfy his woman other than with his cock! Tongue, fingers… there are many options. The most important thing is to redefine your idea of “sex.” For ML and I, we end up having sex all day long – for us, those hugs and kisses and loving touches are all part of us having sex.

With that said, I understand the desire ML has for a nice hard cock deep in her pussy. When she wants this, we have toys that we can use to satisfy this need. But sometimes, she just needs to feel my flesh. In that case, she unlocks me and uses my cock but doesn’t allow me to cum.

There are plenty of ways for you to get yours without letting him get his. 🙂

Mail Chastity has become a very popular subject on the blog. We’ve gotten lots of questions, either through email or Twitter, and we plan on doing more of these posts in the future. We could always use more questions to answer, though, so don’t hesitate to ask us anything!

He Said, She Said/Mail Chastity: Hurts So Good?

Posted by JonMustWait on December 9, 2014
Posted in: Mail Chastity. Tagged: , , , , , , . 4 comments

We recently received the following comment on one of ML’s posts, specifically her post on breath control. Here is the comment from Dedicatedtoher:

Please explain to me how you can get sexual pleasure from hurting someone you love/ Where is the pleasure , the joy in hurting him? Even if he is a masochist, you have the ability to step back and say: “This I cannot do. I get no pleasure from hurting you” Your sexual thrill from inflicting pain on your husband is something I find difficult to understand. I am happy sadism does not work for my wife and I

Both of us have things we would like to say in response to this. So here is your “He Said, She Said” installment of “Mail Chastity” (or vice versa, whichever tickles your fancy).

Lady M: Thank you so much for your comment and question.  I would like to first point out that I do NOT like to hurt my husband nor do I get pleasure from it. I do love his reaction to some slight pain like pinching nipples, nails on his back or balls or even a spanking. I do believe those are all pretty common ways people create a pain sensation to get a reaction from their partner. As I said, I do not enjoy actually hurting him whatsoever. Since it is the Breath Play post in particular that you are referring to, I want to say that at no time during our play like this do I hurt or intentionally cause him pain. If that were to happen, with a misplaced thumb or something, I stop immediately and adjust. I’m actually terrified of accidentally hurting him and often cut play short sometimes. Breath play is not about pain and has everything to do with the control of his consciousness. That I do love, I love the control I have over him. I love seeing his glossed over eyes as he is slipping off into his dreamy state. That does give me a sexual charge and my crotch is instantly sopping wet and drippy. It really is not painful to experience this but rather relaxing and calm I would imagine.

I hope this helps explain it a bit and as I always say, not everyone will ever enjoy the same things when it comes to most things in life. Although… maybe bacon… everyone, except Cagemonkey, likes bacon! 🙂

Cagedmonkey: First, let me say thank you for the comment. It’s a great question, but I’d like to thank you for being so respectful. Although you may not understand or agree with the things we do, I appreciate your mature attitude towards addressing it. 🙂

I’ll start by saying that there is a big difference between “pain” and “hurt.” When ML pinches my nipples just a teeny bit too hard, that’s pain. When she leans the wrong way and kneels on my ankle or whatever, that hurts. I don’t get any sexual thrill from being hurt. Pain, yes, I find exciting. But there have been instances in the past where ML has accidentally hurt me, and we’ve stopped immediately and addressed the situation (and most likely laughed it off afterwards).

The pain itself isn’t a turn on. What turns me on is the control that is involved. ML can make me feel whatever she wants me to feel; whether that be pleasure, pain, or anywhere in the middle. I love that she can cause these sensations, and I love that I cannot fight them.

With all of that said, the asphyxiation/choking/breath play isn’t as painful as you may think it is. Again, it’s about control: My Lady controls my air supply, and along with that my ability to stay conscious. It’s actually somewhat peaceful, slipping away slowly like that. The worst thing I’d say I experience is fear as I get closer to blacking out, but I trust ML absolutely and completely.

I hope this helps shed some light on why we find this type of play erotic and exciting. It’s definitely not for everyone, but no kink really is. What works for us may not work for you. But what’s important is that it works for us. 🙂

Mail Chastity: Female Chastity

Posted by Michele on November 10, 2014
Posted in: Mail Chastity, Tease/Orgasm Denial. Tagged: , , , . 5 comments

Ok so this was actually a comment on the blog and not really mail but this is a better way to address it. I’m sure there are a few people out there who’d like to know.

pcguy asks:
“One question though.. You’d talked about the possibility of maybe eventually trying a bit of “female chastity” as well.  I saw you had the one brief stint of orgasm denial for Lady M, but do you still consider trying an actual device for any period of time at all?  I’ve always wondered if the female devices are really even that practical…”

As you know cagedmonkey and I do, very rarely, have a bit of the “Switch” in us. I’ll be honest and say it’s a controlled type of switch meaning it’s something, as the dominant one, I’m allowing him to do. I love when we do this because once in a freaking while it’s nice to not HAVE to be in control of every damn thing. The other part of that is that I actually do like to experience “the other side” of things. I like to know what it’s like to be on the receiving end of things. It also helps me to know how to be a better Domme! 🙂

The answer to your question pcguy is yes, we do still plan to lock my sexiness up in a female chastity device. We wanted to do it right and not buy some novelty item off Amazon, so we ordered a custom sized locking one. It’s not a true custom device it’s just one that will fit my size, since I’m pretty sure with my huge tits people realize I’m not some nasty pencil thin model chick. It is a black leather device that requires three padlocks to even keep it on and closed. If I could find it right now I would post a pic, but it’s packed somewhere.

So, why haven’t we used it yet? Well first… we need three locks lol and didn’t have them right away, second we ended up moving and third we started to really think about the practicality and logistics of it all. Could I possibly wear it and function – it’s nothing like just having a cage locked on your cock. I mean seriously, every morning after my second cup of coffee who wants to be unlocking 3 padlocks while I’m about to burst?! That and I can literally think myself into an orgasm so the device is really about keeping me from sex… I have to mentally stop my orgasms.

So far it’s been hard to work out how we would actually do it properly. We did come across another device that is slightly different. That device could make these things happen a bit sooner. I will be honest and say that I would never be locked up like my cagedmonkey. Mine would definitely be short term compared to his! I have this fear that if I suppress the horny it might get pushed so far that I lose it again… no one in the world wants Lady to lose her horny!

I hope this answers your question and I thank you for asking. 🙂 please let us know if you have any other questions.