Tag Archives: chastity keyholders

5 Things I Already Love About My New Keyholder

Is Amanda the way a permanently satisfying keyholder relationship lies? I’m beginning to think so after discovering 5 things I already love about my new keyholder.

I’ve only just met Amanda and we don’t begin until December 1, but I’ve already learned a handful of things about her that cause my hopes to soar that I’m headed for a permanently satisfying keyholder relationship.

Finding an ideal remote keyholder often feels like you’re on a quest for the holy grail. And all too often, just when you think you’ve found it, something dashes your hopes. That happened with Lucie. She suited me perfectly, yet after too brief a time, Lucie had to step away from keyholding to attend some pressing personal matters in her real world life. What I had hoped would become a permanent arrangement, failed to materialize.

My first attempt at finding a new keyholder hasn’t worked out the way I had hoped. The chemistry just hasn’t developed. Since it has become increasingly difficult to find potential online keyholders the way I’ve done it in the past, I turned to the Chaster app. And then I met Amanda.

After a couple of chats, things already looked positive. But with 9 days left to go with NNN and my liaison with Michele, to my surprise Amanda isn’t just sitting back waiting for December 1. She has stayed engaged with me and we’ve chatted every day since we met. Amanda continues probing me for more information, not only about the things I like, but why I like them, and how they make me feel. And in the process, I’ve discovered five things that I already love about my new keyholder.

Amanda Really, Really Loves Chastity

Yesterday, Amanda gushed about how much she loves having full control over a man’s penis and his “primal” urges for sexual pleasure and why. Having complete dominion over a man’s erections and orgasms. In fact, she warned me if we continue together after the 7-day trial we’ve agreed to, I should prepare myself for permanent chastity. Here is why I feel this is so important.

There are lots of different views about male chastity from the perspective of dominant women. As I’ve seen in many Fetlife community discussions, it seems most dominant women are completely indifferent about if not outright hostile to the idea of male chastity involving the wearing of chastity devices. While some tolerate or fully embrace the idea of keeping their man locked up, many others absolutely despise the idea of their man wearing a chastity device.

While the latter, as femdoms almost universally do, insist on orgasm control and controlling their man’s access to sexual pleasure, they insist a man should be fully capable of controlling himself and doesn’t need a piece of metal or plastic locked on his genitals to do it. He only needs to obey his dominant. And, they add, no chastity device is foolproof and totally effective in preventing a man from having an orgasm. Many of these women see chastity devices simply as toys catering to yet another silly male penis-centric fetish interest and want nothing to do with it.

Even among some of the pro keyholders I’ve had, I quickly realized they felt no genuine interest in chastity and only offered keyholding because there are men willing to give them financial tributes for doing it. None of those experiences felt very enjoyable. So, it is important to me to have a keyholder who is as serious and passionate about chastity as I am, and Amanda definitely ticks that box.

Amanda Seeks a Permanent Relationship

The second thing I love about Amanda is she has told me from the start that she wants another full-time submissive man. She offers temporary chastity locks on the Chaster app, but she offers the week of consideration we’ve agreed to only to someone seriously seeking a full-time Domme. And that is exactly what I’m looking for, a permanent arrangement, so I can put the days of looking for another keyholder every few months behind me. I found a lot of benefits from self-locking in the past, but after my experiences with Lucie, I know I now want chastity controlled by a dominant woman. I really can’t imagine going back to self-locking anymore.

Amanda is an Actual Domme

Like Lucie, Amanda is an actual Domme with IRL experience in her local kink community. And again, from experience, I know women like Amanda offer a more comprehensive and meaningful dynamic than those women who only offer online chastity keyholding services and have little interest or experience with the wider world of kink. There is greater variety in the dynamic with an actual Domme who has done more than just online keyholding. That’s because they seek not only to enforce someone’s chastity, but want to explore their own kinks, desires, and needs with a submissive partner. That only makes chastity more meaningful for me because I want it to be focused on the keyholder.

Chastity, with a keyholder for me, has never been something where my greatest interest was only getting my own kinks satisfied. I don’t see a Domme as a kink dispenser. I have far more respect for dominant women than that. It is vitally important to me that my keyholder also gets her desires and needs satisfied and not just through financial tributes. I believe already that Amanda will offer that opportunity.

Amanda Is a Generous and Caring Person

Even with knowing her only a short while, Amanda has already shown to my satisfaction she is a generous and caring person. I have already remitted the small tribute she required for the 7-day consideration lock and I wouldn’t have faulted her at all had she chosen not to engage with me until December 1 once we closed the deal. She already had a list of my kink interests, limits, and toys to use for designing the tasks she will give me to do. But she didn’t do that.

Aware of how little I paid for the 7-days, I felt no entitlement to her attention until we start on December 1. But Amanda has started conversations with me every day, generously giving me her time and attention out of her interest in getting to know me better. Her interest in me as a person has been so clear. She reminds me quite a lot of Lucie in how generous and caring a woman she is. And that impresses me so much.

We Share Many Common Kink Interests

I’ve learned during the past week that Amanda and I share many other common kink interests besides just chastity. No, we don’t match perfectly. No two unique people ever do. As one example, I think Amanda enjoys enforced feminization a great deal more than I do. I’m fine with it in moderation, the way Lucie used it for the mild humiliation effects it has on me. Feminization just holds no appeal for me since I’m not a sissy-type submissive man and I’m not into CD. Nothing wrong with any of that, but I don’t find behaving or dressing as a woman arousing in the least. But Amanda has already gained my trust that she will respect my limits and will compromise even on things she finds interesting and fun to explore. And, based on our conversations, I feel we have enough common interests that neither of us will feel bored or short-changed.

 

Honestly, meeting Amanda has made NNN more difficult because I’m so excited for December 1 to arrive that I can’t wait for NOvember to end. Maybe I haven’t met Lucie’s equal, but the more I get to know Amanda, the more I feel convinced I’ve had the good fortune of meeting another special Domme.

 

31 Days of Chastity Meme Day 24: Partners

While I think having a romantic partner as your keyholder is always the best situation, relying on professionals has advantages. For one, you can choose a professional with the qualities you most desire. In today’s 31 Days of Chastity Meme Day 24, I’m sharing what I look for in a keyholder.

What qualities do you look for in a keyholding partner?

Having had what I think is a representative sample of professional keyholders, I know they aren’t all the same. I’ve talked to several others who I ultimately chose not to enter keyholding agreements with when it appeared obvious they didn’t possess enough of the qualities I was looking for. But here, I will not focus on the shortcomings I’ve observed, but will instead share what I look for in a keyholding partner.

Authenticity. I look for someone who has a sincere interest in the chastity dynamic, not someone who only offers keyholding as a side gig to earn some extra money. Those types rarely have a professional website and instead rely on X (formerly known as Twitter), Fetlife, or one of the many fan sites to attract clients. Someone sincerely interested in enforcing chastity will have a lot of knowledge about it. Those only interested in making money usually don’t. A Professional website and knowledge of what chastity is about are the first things I look for.

Legitimate Dominance. I also look for a keyholder who is legitimately dominant. A romantic partner who graciously agrees to become a keyholder may not be a legitimate dominant or perhaps just hasn’t discovered the dominant part of their nature at the beginning. That’s okay. But when you tribute someone to enforce your chastity, you have every right to expect that person is a true dominant, not someone simply playing a role. I think I’m pretty good at sensing true dominance, but the best ones seem to exude dominance from their pores. Lucie is a good example. Five minutes into our first video call, I had no doubts about whether Lucie was the real deal or not.

Confidence. I look for confidence in a keyholder partner. Intuitively, you might think authentic dominance and confidence go hand in hand. They don’t. Confidence is usually a product of knowledge and experience. Someone who seems to project the “ultra bitch” or “psycho cunt” image intentionally are red flags for me because I know that is usually how someone lacking confidence attempts to hide it. Think Kamala Harris. Sorry. Nothing personal and I have no idea if she considers herself dominant, but she is the epitome of exactly what I’m talking about here. Exercising control requires confidence. Faking it doesn’t cut it.

Caring. I want a keyholder who cares about me as a person and shows it. A domme can be strict and even impeccably cruel and still be caring at the same time. She can be stern, bossy, even tyrannical. I want all that as long as she is also caring and makes me feel she has my best interests at heart.

Fair. I have dealt with dominant women who thought exercising dominance meant tricking or baiting a submissive into technical violations of their rules so they had an excuse to administer punishment. That doesn’t work for me. I expect honesty and fairness. Respect goes both ways. A dominant should give clear instructions, all questions for clarification if necessary, and then enforce fair standards. I don’t expect to be coddled, but I do expect fairness and I wouldn’t hesitate to end a relationship  with any dominant who seemed to believe playing stupid games was what dominance is about.

Intelligent & Creative. I think intelligence and creativity are important qualities to seek in a keyholder. This is always true, but especially true with distance keyholders. Having a keyholder who doesn’t have these qualities severely limits the length of a relationship because you will soon exhaust what can be done online. Things will then quickly grow stale and both parties will grow bored and one or both won’t want to continue.

A Sense of Humor. One of the things I’ve treasured most about Lucie is her sense of humor. Chastity should be fun. Lucie makes it fun. As an example she has often assigned me a task with the requirement to send her a video of my performance. More than once she has given me a task that she knew very well was impossible. And when I contacted her, frustrated after learning I couldn’t do what she asked because I realized it was impossible, she would laugh and admit she knew it was impossible. And no matter how frustrated I was, I’d always end up laughing right along with her. Chastity doesn’t have to be and shouldn’t be deadly serious all the time. It should be fun for both parties to a keyholding agreement.

Those are the qualities in no particular order that I look for in a keyholder partner. I’m enough of a realist to know you aren’t often going to find a keyholder who possesses every single one. But I won’t settle for a keyholder who doesn’t have at least most of them. With Lucie, I’ve been exceptionally lucky because she ticks every box. That’s why I hate the thought of our relationship ending. It’s unlikely I’ll find another keyholder keyholder who will offer anything close to the experience Lucie has given me for the past five months.

Tomorrow in the post 31 Days of Chastity Day 25, I’ll offer my thoughts on the subject of openness about the practice of chastity. Hope you will join me again as I respond to this prompt:

How open are you about your chastity and being locked up? 

31 Days of Chastity Meme Day 4: Partners

Here on the 31 Days of Chastity Meme Day 4, the discussion centers on partners.

Did you ask a partner to lock you in chastity, or did she/he suggest it to you? Write about that first conversation.

I edited Tickleberry’s original question for today to fit my circumstances. They aimed the original more at those whose wife or other partner acts as keyholder. If you’ve followed this blog at all, then you know I have only had professional keyholders, including the one I have now, my long distance Domme Lucie. So, obviously, I asked all of them to lock me and, in return, gave them a financial tribute to enforce my chastity. That’s a fair arrangement, if you ask me, and the arrangement that works best for me since I’m not in a relationship and am not looking to get into one.

Lucie is unique. In the past, I have engaged a pro keyholder whenever I felt the need for a break from self-locking. Except for my very first keyholder and Lucie, those were only one-month commitments, and afterwards I returned to self-locking. That’s what I had in mind when I first applied to Lucie for keyholding services. But my relationship with her has been so amazing I haven’t wanted to end it. The chemistry between us only grows stronger, and I’m not sure I ever want to end it. On 9 October, I will have been with Lucie for five months.

Our relationship has changed a lot since my first time with Lucie. That’s because we have become well-acquainted and she knows me much better now, what things turn me on and make me feel submissive and which ones do little of either. While she is still very strict, which I love, she isn’t as mean to me as she was at the start.

We have a lot of kinks in common, so most things Lucie tasks me to do are things I enjoy as much as she does. I’ve even come to like some things Lucie enjoys I wasn’t particularly crazy about at first, because it has become so important to me to please her. Lucie and I understand each other and respect each other’s boundaries. She was very clear at the beginning our arrangement wasn’t a boyfriend-girlfriend thing and that was great for me because I wasn’t looking for that. Not to mention we live on different continents.

Having had more than a few unpleasant experiences with guys she played with becoming infatuated with her, Lucie kept things strictly professional at the beginning. But now that she has gotten to know me better and we’ve built trust, she treats me more like a friend. Not to say she has relaxed any of the boundaries that exist naturally between a Domme and her sub. And I wouldn’t want her to do that.

Compared to the other professionals I’ve played with, the tributes Lucie asks for are so minimal. Especially since she also puts so much more time and effort into our dynamic than any previous keyholder that I’ve had ever did. In fact, she often extends our play far beyond when it has been due to end. For example, our session (for lack of a better term) before Locktober was supposed to last for one month. Instead, Lucie kept extending it until eleven weeks had passed by the time September ended and Locktober began. Even though I twice offered to tribute her for the extra time, she wouldn’t allow it, saying she enjoyed playing with me and said, “naturally you pay less.” I feel a little conflicted about it, honestly. Yes, I appreciate her generosity, but I know the time and attention Lucie devotes to me is time and attention someone else could pay for. But it’s her decision. I’ve strayed from the topic at hand, so let’s get back to it.

While I haven’t had the experience that many guys have had, having to figure out some way to bring up their desire to a wife or other partner, I did have a conversation with Lucie at the beginning during which I’ll bet I felt just as nervous. Ours took place on a video call and I had to explain why I felt an attraction to chastity, share what other kinks I was interested in and enjoyed, and list my hard limits. Lucie listened intently and asked questions about the things she wanted to know more about.

Not that every guy would feel this way, but I found it far more embarrassing spilling all my kinky secrets face-to-face to a perfect stranger, a drop-dead gorgeous stranger at that, than I would have had discussing it with someone I’d seen naked and had sex with. But Lucie was great about it, although she now uses everything I told her against me when teasing me. But the discussion was important because Lucie needed to know what type of submissive I was.

There are many types of submissive men, ranging from rather mild to rather extreme. While the stereotypical view of submissive men are that they are weak and unmanly, even effeminate, it takes strength and courage to give up control and submit to another person. And Lucie understands that. She also knows not all submissive men want to wear women’s clothes or to become a sissy. Not judging any of that, but I’m not that type of submissive guy. While I desire to put my dominant’s desires and pleasure before mine, I prefer to remain in my natural masculine role. Yes, Lucie sometimes uses that against me too for laughs, but she never tries to emasculate me. Part of it is she knows what works and what doesn’t in leading me where she wants to take me. But I think Lucie prefers masculine men because she finds persuading them to submit to her far more satisfying.

That wraps the discussion for this fourth day of the 31 Days of Chastity Meme on this fourth day of Locktober 2023. Hope you will return tomorrow when I’ll share about my first time locked in chastity in response to these questions:

What was your first time in Chastity like? How long were you locked? What did it feel like and what happened on your release?

Looking for a Last Minute Locktober Keyholder?

With Locktober only a week away, time is growing short to find a keyholder for those who don’t want to go it alone. So, I thought I would pass on an interesting opportunity that I just became aware of for anyone who might be interested.

Having done Locktober both ways, self-locked and with a keyholder, I know from experience the latter is much more enjoyable than the former. If you’re planning to do Locktober this year, but haven’t found a keyholder, perhaps M. H. Macdonald can help you out.

Femdom M. H. Macdonald is best known for her entertaining chastity and female domination fiction books, but this year she is offering keyholding for Locktober.

The service is NOT free, so if you are a staunch believer in not paying to play, you can stop reading now. But for those not against paying for keyholding services, Macdonald has made an interesting offer. Instead of paying a direct tribute, all interested guys must do is buy $31.00 worth of her books and provide proof of purchase, and she will supervise your Locktober lock up. At only a dollar a day, that is about as cheap as paid keyholding services get.

Rest assured, M. H. Macdonald knows her way around a chastity device. She is a dominant woman with a submissive partner who she keeps locked in chastity. And anyone who can write such entertaining and detailed femdom fiction has all the imagination and creativity a good keyholder needs. Since I haven’t had her as a keyholder, I can’t very well offer an unqualified endorsement of M. H. Macdonald. But I will say I’m confident enough of her abilities that if I didn’t already have a Mistress, I would be more than willing to try Macdonald’s service which I think is a generous offer.

This deal seems like a win – win. Those who enjoy femdom and chastity fiction will get some entertaining books to read plus the keyholding and M. H. Macdonald will sell a few books, something all authors enjoy. Most of the books sell for $2.99, with a few priced at only $1.00. So a guy would need to buy around ten titles to meet the $31.00 threshold. Also, you will need a FetLife account since that’s where Macdonald is accepting applications and the platform she will use to enforce the chastity of successful applicants.

I suggest you first message Macdonald on FetLife to express your interest before purchasing the books to make certain she has room for you.

 

Summary of Macdonald’s offer:

  • Contact Macdonald by DM through her Fetlife page to apply.
  • Purchase $31.00 worth of her femdom/chastity fiction books on Amazon. You can find a complete list of her books here (twenty-eight titles so far).
  • Send a second DM with your proof of purchase (Amazon receipt).
  • Lock up on October 1 and submit the required daily proof of lock photos to Macdonald throughout Locktober. (Macdonald requires either the use of a numbered plastic lock on your device or a lock box with a timer lock to secure your keys).

 

For complete details of Macdonald’s Locktober keyholding offer, read her post on FetLife here. (Free FetLife membership required to access).

If anyone uses Macdonald’s Locktober keyholding service, I would be grateful to hear about your experience with it and am happy to post any reviews anyone will share.

 

Disclaimer: I have no commercial affiliation with M. H. Macdonald beyond being a fan of her fiction books I’ve purchased with my own money. I received no gratuity or other consideration from Macdonald in connection with this post.

Why I Prefer Having a Pro Domme Enforce My Chastity

I’ve made no secret of the fact that I prefer having a pro domme enforce my chastity during those times I’ve wanted a keyholder. Mostly that is because of two reasons.

AI art by Chaste

I am not in a relationship with anyone and haven’t been for several years now. I don’t have a wife or girlfriend who might enforce my chastity, though I’ve always believed that is probably the very best way to do chastity. The reason I’m not in a relationship and not looking to get into one is the other explanation for my pro domme as a keyholder preference.

Several years ago, I went through a very painful break up with a woman I had expected to spend the rest of my life with, and I’ve never fully recovered from it. I had two relationships with wonderful women after that one ended, but that’s when I realized relationships would never work for me again because I had loved that one woman so completely and so deeply that I simply had nothing left to give to another. Getting involved with another woman would never be fair to either of us, because any new relationship would ultimately fail.

That also explains why I’ve never considered seeking what many term a lifestyle domme as a keyholder, a dominant woman who might enforce my chastity as part of the power exchange and exert other forms of control, all with no expectation of payment. I have great respect for the lifestyle dommes I know, a few of whom I count as friends. But a relationship with a non-pro domme means you must deal with the dominant woman as the whole woman.

Many of the same challenges you face in vanilla dating and relationships are in play with a lifestyle domme. And that is exactly what I don’t want and firmly believe I won’t ever want. Satisfying romantic relationships is part of my past, not part of my future. Yes, it sometimes makes me feel sad to think about that, but as a realist, I can’t question the truth of my convictions.

A pro domme, in comparison, is not looking for a relationship or even any sexual interaction. Not to say that she won’t require you to perform sexual acts that she might also find arousing to have you do, or that real intimacy can’t naturally develop between the two of you. But she will never be your girlfriend.

A pro domme may be as keen about chastity enforcement and teasing and denial as you, but she is providing professional services and is in the business of creating and delivering immersive fantasies. She will connect with you in much the same way as a personal trainer, therapist, or life coach, providing her services for a fee (tribute).

I’ve discovered that many people know very little about pro dommes, what they do and don’t do, and what submitting to a pro domme is actually like. What has surprised me the most is how little lifestyle dommes know about all that.

Some assumptions about pro dommes I’ve seen lifestyle dommes post on blogs and other places were shockingly false. One example I’ve read was, “Pro dommes are the closest you can get to a porn-on-demand experience.” This woman, as many others do, believe pro dommes are “kink dispensers” that give you exactly what you want because you’re paying them. Having engaged a half-dozen pro-dommes, one of whom is internationally known and respected, I can tell you they are not kink dispensers.

I’ve never had a pro domme ask me, “So, what do you want me to do to you?” Yes, they want to know what you’re into because they aren’t mind readers. But they only want to know what your kinks are in broad terms and what your limits are. Like, “I’m into chastity, teasing and denial, impact play, and anal play. My limits are public humiliation, feminization, and cross-dressing.” They don’t care about and don’t want to hear about what you specifically want them to do to you.

Try telling a pro domme, “I want you to lock my cock in a chastity device for a week, then unlock me, and then give me jack off instructions while you watch me masturbate, and then…” You won’t even get that far before they shut you down.

Sure, you can probably find a cam girl on Only Fans who will do all that stuff for you for the right price, but submitting to pro dommes doesn’t work that way. They will take your kink interests and decide where yours overlap with theirs and then, while respecting your limits, will deliver an experience that addresses those shared interests in whatever way that pleases them. Just because you’re tributing them doesn’t mean you get to be in charge. It also doesn’t mean they don’t expect to get pleased or get their desires met too. That’s what dominance and submission are about. It’s an exchange.

Tributes are a funny thing to me. I have no trouble at all tributing a pro domme. A tribute shows respect for a pro domme’s expertise, time, and attention, all of which she could devote to someone else if she wasn’t giving it to you.

A financial tribute to a pro domme is not like paying a prostitute for sex. It isn’t like paying a woman to date you. A pro domme will not have sex with you because she isn’t a prostitute and she won’t be your girlfriend. They are not “findoms.” Yet I see guys all the time on forums advertising for a keyholder who always adds, “Not looking for pay-to-play.” Yeah, good luck with that.

If you want a domme, don’t want to tribute a pro domme, and expect free keyholding, then stop wasting your time posting personal ads on chastity forums. Find out where your local kink community hangs out, get plugged in, and start meeting some dominant women and you might get lucky by finding a lifestyle domme who is interested in you. Or else find someone who isn’t necessarily dominant but willing to date and explore chastity with you. Most women, even vanilla women, can be great keyholders as long as they want to be keyholders.

I’ve had some uniformly wonderful experiences with the pro dommes I’ve engaged with. For the past four months, I’ve submitted to the best pro domme I’ve ever played with, Lucie.

I am still enough of a romantic in the sense I don’t want to submit to just any random domme. I want that connection to one person. And I want that connection with Lucie after learning how well I respond to her relentless willingness to bend me to her will. She doesn’t indulge my kinks. Lucie uses them to taunt me with her power. She enslaves me with her body and her desires so that all I think about is the best way to please her. Even when offering what pleasures she permits me, she is only reminding me how completely she controls me. I want the relationship with Lucie to last.

Lucie has already helped me discover so much about the parts of my sexuality that exist outside what I’ve fantasized about, and she has unlocked the submissive part of my nature in ways I didn’t realize were possible. The vulnerability of being submissive is ultimately part of being a half of a whole. And in the power exchange dynamic of D/s, Lucie, for me, has become the other half.

My pleasures, like my kinks, belong to her. They are the tools of her control. “My pleasure doesn’t matter” has become my mantra. I never expected submitting to Lucie to impact me this much, to feel so bonded with her, so in the beginning, it felt bewildering to feel that things were far more real than I had expected. But she has transformed me into her perfect, driven, obedient boy.

Every opportunity to serve, to sacrifice, to suffer for her feels like something relevant has passed between us. Each whimper and groan from my heightened physical arousal produced by her vivid sexual creativity makes me feel gooey inside. “Good boy” still provokes those same shudders of desire as when I first discovered those words were in Lucie’s hand, a leash on my soul.

Those are the reasons why I prefer having a pro domme enforce my chastity. Or, to put a finer point on it, why I prefer having Lucie enforce my chastity. She has left an indelible mark on my soul.

 

She Loves These Edges

Lucie sets a lot of tasks for me to do for her. Amazingly, each task has been unique. I’ve yet to do the same one twice. Well, with one exception. Lucie makes me do a lot of edges, far more than I’ve ever done in my life. It wasn’t long after she became my keyholder, whenever I was edging, that this thought occurred to me. “She loves these edges.”

"He hates these cans," but she loves these edges

It isn’t unusual for a keyholder to require her charge to do edges. Just recently, I read an article that said edging is the most popular teasing technique used by chastity keyholders. I’ve had several remote keyholders who made me edge, but none were ever as enthusiastic about making me edge as Lucie is.

Though it seems unlikely that anyone reading this isn’t aware of what edging is, I’ll pause here to offer a simple definition. Edging is the practice of stopping sexual stimulation of the genitals, just short of reaching orgasm.

Some use the practice alone or with a partner to prolong a sexual experience and to build to a more intense orgasm through delay. But for those of us who wear a chastity device who have a keyholder controlling our orgasms, edging is a cruel teasing and denial technique often applied by touching a powerful vibrator against the chastity device cage.

I admit I have a love-hate relationship with edging. Yes, the stimulation from a vibrator against the cage feels intensely pleasurable and edging truly makes me insanely horny. But there is a downside. Edging also leaves me feeling maddeningly sexually frustrated when a session ends. Lucie, of course, knows this very well, which is why she makes me edge so often. In fact, she usually reserves two days each week only for edging. And sometimes, she whimsically texts me out of the blue and tells me to stop whatever I’m doing and to do some set number of edges for her entertainment.

In the past, I used a powerful corded Hitachi Magic Wand against the cage for edging. It is very intense with any cage, but especially so with the Kink3D Cobra I’m wearing now. Mostly, I did the number of edges Lucie prescribed with a 30-second pause between each one, and then texted her when I was done. Sometimes she required me to send her a video while I edged to prove I was doing “proper edges” by getting really close before stopping the stimulation.

Edging with the Hitachi makes the cage contents try to get hard, and the erections push the cage several inches away from my body, as far as the base ring around my balls allows. This causes the base ring to exert a lot of uncomfortable pressure on my balls, something Lucie never tires of hearing about. And usually, before I’ve completed the second of ever how many edges she has demanded, I’m leaking. That’s another thing Lucie loves, and something she demands to see when she requires videos.

But now, we’re doing the edges differently. Recently, Lucie told me she had a new idea for making edging much more fun. What Lucie calls a new “idea,” I affectionately term a new “devious scheme of torture.” But I never say it out loud. So, I was certain she meant a new idea for making edging much more fun for her to inflict on me. The new idea, as her new ideas often do, involved me adding a new item to my once modest sex toy collection that is now growing out of control like a California wildfire. The item she asked me to get was a new cordless wand vibrator.

“But I already have the Hitachi,” I countered cautiously. “And I doubt a cordless will be nearly as powerful as a corded Hitachi.”

“Yes, those are great, but this is a powerful cordless vibe,” said Lucie. “And I want it because I will be able to control it remotely with an app on my phone.”

Well, okay. I had to admit that part of it intrigued me. I already have some anal toys I bought at Lucie’s suggestion that she controls remotely with an app on her phone. And I sort of like it when we play with those. So I ordered the vibe she wanted. Have I mentioned that I have difficulty saying no to Lucie?

Anyway, now on the two days each week reserved for edging, Lucie controls everything. My role is to hold the vibrator against the cage where she wants it. Then, while monitoring the edging with a video call made from her Mac, she controls the intensity and the patterns of vibrations with the app on her phone. All well and good. I do like the new way since Lucie is edging me. It feels as real as it gets with virtual, and somehow it feels quite intimate. But, of course, Lucie the sadist, always has to push the envelope.

The first time we used this new edging method, she began by needlessly reminding me, “It’s your responsibility to tell me when you’re at the edge, so we stop in time. If you cum, that’s your fault, and I will punish you severely.”

Trust me. Lucie doesn’t use the term “severely” lightly. She means it. Harsh punishment. Punishment to an undesirably great or intense degree, usually directed at the most vulnerable part of my male anatomy.

“Yes, Mistress,” I said, already suspecting there was some cruel reason behind the needless reminder. The thin smile on her lips and that familiar look in her eyes suggested I was about to experience some new form of torture.

Lucie activated the vibe after directing me to press the massage head against the tip of the cage where it meets my balls, the place where I feel the vibrations most intensely. Maybe because I was already so horny combined with the novelty of Lucie edging me, I got to the first edge faster than usual.

“I’m close, Mistress, please stop.”

When the vibrations continued unabated, I glanced at the screen and that’s when I saw that smile. That smile that always strikes terror in my heart. That sadistic smile.

“How close?”

“I’m at the edge. Stop, please, Mistress.”

“Ask me nicely.”

“Grr… please stop, Mistress. Please!”

“Beg me to stop.”

Okay, I might have used some bad words, followed by some frantic begging, followed by a desperate shouted, “You’re going to make me cum if you don’t stop now!”

Mercifully, the vibrations stopped, but for a moment I feared not soon enough. I felt those little tremors in my groin that usually herald the start of the muscle contractions that occur at ejaculation. But, thankfully, I didn’t cum. I only leaked.

“Mistress, you almost made me cum,” I whinged.

“Why can’t you be a man for once in your life, sissy boy?” she retorted with an evil grin. “Exert some self-control.”

Seriously? Be a man for once in your life? Exert some self-control? That’s the same line she uses when I flinch whenever she makes me slap my balls with a riding crop while she watches on video calls. I knew with six edges to go that I was in for a long session. She loves these edges.

Don’t Say Yes

Keyholders, don’t say yes, too easily or too soon. Sometimes when he begs you to unlock him, what he really wants is to hear you say no, repeatedly and without hesitation.

The secret fear of the chastity sub is that the keyholder may not have the will to keep saying no to the point where he can endure no more. He’s afraid she may unlock him too soon. He has picked her for his keyholder because she is a good woman. After all, it’s an intimate relationship, like any other. He wants someone who feels sympathetic, is kind, and caring. Who doesn’t want that in a partner? But can a woman like that really be the strict, implacable keyholder he craves? One who is indifferent to his whimpers, his half-suppressed appeals for mercy? Can she continue to relentlessly subject him to merciless teasing and the pains of denial?

Some women, especially those who accept the keys to a chastity device from a partner they are already in an intimate relationship with, find it hard not to say yes when he begs her to unlock him. Some even feel it’s cruel to keep him locked when he seems so miserable. After all, she loves him and finds it hard to watch him suffer especially when she feels responsible for his torment. Or perhaps she worries about his prostate health or his comfort. But a keyholder must have the mental strength to keep saying no when he begs, when he pesters her for release, when he whines how miserable the blue balls feel.

What the chastity sub needs is for the keyholder to overpower him, to force him to yield. He wants her to strip him of every last vestige of ego and resistance. He doesn’t want a keyholder who takes pity on him just because he complains about the frustration he feels or because he moans about the ache in his balls.

As the need and the frustration increases, a tension takes hold in his mind. Gradually it approaches the point where it seems unbearable. Soon he wants it to stop. He wants her to unlock him and allow him relief. And yet, and this is the true mystery, he doesn’t want her to say yes. He wants to see how much more he can take. He wants the sort of keyholder who might say to him, “No, I want you to remain locked for a while longer.” What he needs is a keyholder whose desire to keep him locked will ultimately prove stronger than his desire to suffer the frustration of no sex, no orgasms, no access to his penis.

Indeed, sometimes when he wants to stay locked in chastity, he will still beg her to unlock him and allow him respite. He is simply asking because he wants to her say no, without hesitation because he craves feeling her exert her control. And if he pesters her until she relents, he feels only disappointment. He wants to know she won’t say yes too soon, that she won’t let him off lightly.

Sometimes, in the cold light of day, he contemplates the full implications of his desires and feels a little frightened by it all. Surely, he doesn’t really want this. He needs a safe word. He needs her to clearly understand when he’s reached his limits. He needs to know he can bail out if it gets too tough. But there is a part of his mind that doesn’t want that at all. The thought that she might have the power and will to push him beyond what he can bear makes his head swim. It makes his dick throb within the confines of its unyielding cage and drool precum. When he handed her the keys, he wondered. “Have I finally met my match?” He hopes so. “Please,” he prays, “Don’t say yes when I beg.”

Yes, while he stays locked and suffers the pangs of need and frustration, he wants her sympathy, her soft caresses, and soothing words. Most of all he wants assurance she recognizes how much he is suffering for her. But right now, he doesn’t want release. He wants to plumb the depths of her cruelty. Make her unyielding. Make her relentless.

The Critical Difference Between Chastity With a Key Holder and Self-Locking

As mentioned in the previous post, I engaged a Professional Dominatrix as my key holder for the observance of the longest day (month-long observance of International Male Chastity Day). Four days into it (I started a day early), the experience of having a key holder has reminded me once again of the critical difference between chastity with a key holder and self-locking. It’s the control.

I spent the entire year of 2021 self-locked and had to look back at my notes to see when I last had a key holder. It was June through November 2020. The benefits of wearing a male chastity device are so obvious that I willingly self-lock. That’s also why I recommend practicing solo male chastity to other single guys without hesitation. It’s still fun and meaningful. You still get many of the benefits. But we don’t get one element of chastity when we go it alone. We miss out on one of the most satisfying aspects of chastity, the experience of surrendering control to another person.

Surrendering Control is a Common Male Fantasy

Many men (if not most) fantasize about giving control of their sexual desires over to their wives, girlfriends, or partners. This dynamic, commonly known as power exchange, requires complete trust and open, honest communication. Many men enjoy being more of a passive player when it comes to sex, taking on a sexually submissive role. It runs contrary to the way they experience their lives outside the bedroom. So, they enjoy the idea of a partner locking up their penis, teasing, denying, and deciding when they can orgasm. It’s about feeling like you surrender control.

In the beginning, the novelty and excitement are heady and arousing, but once a little time passes, the frustration builds, and you must dig deep to find your own power and strength of resolve, as the temptation to beg and plead for release ramps up. It took only four days under the firm hand of my Mistress to remind me of all these things and how much I’ve missed it.

The Effects of Control

I’m not at the frustration stage yet, probably because I have acquired so much experience wearing a cock cage. But here is how the control of another person is making itself felt. Right now, I am super horny. That’s my preferred state, although it can be massively distracting. Sure, I get horny sometimes when I’m self-locked. But it never feels this intense.

The other thing I’ve noticed is attempted erections waking me during the night. I adjusted to the nocturnal erections a long while ago, and they rarely wake me anymore. But last night, attempted erections woke me three different times. That isn’t ordinary for me. All my custom cages are designed to fit tight with no extra space, so they all do an excellent job of stifling erection attempts quickly. Also, I woke up this morning with morning wood. Since my Jail Bird offers no extra space for the contents to grow, the boner pushed the base ring and cage a good distance away from my body until it subsided.

These are the things that make me aware of the control. Is this mental or physical? I think maybe a little of both. When you’re self-locked, even when you have no intention of unlocking, it’s always there in the back of your mind that you could unlock if you wanted. But it removes that option when you have surrendered control to a key holder. You can’t unlock and remove the cage without breaking the agreement and disappointing your key holder. Both are things I’d never do.

I have never experienced having an intimate partner I cared about and knew cared about me as a key holder. But I have no difficulty imagining that is the best possible way to experience chastity.

No matter how charming, dominant, or attractive a professional key holder might be or how over time, you sometimes develop feelings of affection for them on some level, you always understand it isn’t personal for them. It’s just a business transaction. They provide you a service for a fee you feel you need or want.

Nevertheless, the feeling of control it produces is still very real. And I love that feeling. It makes me feel comforted, cared for, and sexy. It makes the practice of chastity all the more profound. The feeling of the chastity device holding me tight and knowing another person has all the control is one of the best feelings in the world.

Ladies Start A Lucrative Chastity Keyholder Side Gig

With the explosion in interest in male chastity among everyday guys, now is an excellent time for enterprising ladies to start a lucrative chastity keyholder side gig.

The Market

There are lots of single guys out there who want to start wearing chastity devices, but they don’t have partners to ask to be their keyholders. Many of them are forced to go it alone. But going solo is hard and not very enjoyable for most guys.

The male brain has only a limited ability to say “no” day after day to something as strong as sexual desire. When a guy must depend on willpower alone to battle the fires in his loins, there’s a good chance he won’t last very long before taking the device off and taking things in hand. This situation presents a massive opportunity for women looking for a profitable side hustle to earn extra income.

While I’ve seen more women offering keyholding for-fee services, frankly, I’m amazed far more women aren’t jumping on the opportunity. That’s why I decided to write this post. I have no idea how many women visit Cut To The Chaste, but I’m hopeful I might persuade those who do to consider starting an online keyholding for-fee service.

What Is A Keyholder, Anyway?

Concisely put, a keyholder is a person who consents to possess the key to someone else’s chastity device physically. With a keyholder, chastity is about a guy transferring ownership of his penis to another. Literally. Once you, as a keyholder has told your client to lock his penis inside a chastity device, his penis belongs to you. It becomes your toy and exists solely for your pleasure and amusement.

You can allow your client to access and take out your toy and use it whenever you like. You can also make him lock it safely and securely back into the cage whenever you deem fit. The keyholder decides when or if a client may orgasm or enjoy sexual pleasure. She controls and denies his orgasms. This is a powerful concept and shows how much chastity and chastity play has a psychological component to it.

Eww, Isn’t Chastity Keyholding Sex Work?

Sure, I get it. Not everyone wants to be a sex worker. Not that there is anything wrong with that. But, holding the keys to a guy’s chastity cage long-distance is not sex work. There are sex workers who do it, like professional Dominatrices and Pro Dommes, but they offer a lot of other sexual-related services to go with keyholding. And most only do chastity play face-to-face sessions with their clients.

Did you know there is a specialist security service business called keyholding where a contracted security firm holds a set of keys to your commercial premises in a secure, off-site location to be used in the event of a security breach? Chastity keyholding is actually quite like that.

Being a keyholder is not about sharing intimate photos or having sexy chats with your clients. No cybersex is required. At its essence, it just about taking possession of and holding the keys to a client’s chastity device.

Of course, if you wish, there are plenty of related services you can offer your clients for additional fees. But any way you slice it, being a fee-based chastity keyholder is not sex work. It doesn’t require complying with a bunch of burdensome laws and regulations, and it’s all perfectly legal.

Why Start A Chastity Keyholding Service Side Gig

Maybe you’ve already been wondering how to make money—more money, that is.
Whether you want to get more aggressive with paying off student loans, digging yourself out of credit card debt, or paying for your next vacation, making extra money on the side is a smart strategy for working toward your goals.

There was a time when you could simply get a part-time job. But, in this era of COVID-19, that’s a lot harder to do nowadays. Also, many Americans have lost their full-time jobs thanks to the pandemic. Sadly, some of the jobs are never coming back.

Consequently, more people are getting side gigs, which allow them to set their own hours and rates. With a work from home side hustle, you’re your own boss, can decide what you do, when you do it, and how much you make.

Those individuals who were already working from home when the virus hit seem to have weathered the storm a little better than people who commuted to work every day. Owning a small business and working from home may be the future for a lot of us in the wake of the COVID-19 outbreak.

Sure, there are plenty of other things you can choose from if you’re looking for a money-making side gig. But, I think you would have to look long and hard to find anything that comes even close to the small initial investment requirement and the upside growth potential of a chastity keyholder service.

How To Get Started

The good news is you probably already have the basics you need to start an online chastity keyholding service—a laptop, tablet computer, or smartphone. There are a few bells and whistles you can add to the basics, but it is possible to get started as a keyholder with no upfront investment.

Some enterprising ladies create a Twitter page and operate their keyholding service entirely on that platform. It doesn’t cost them a cent. That can work, but don’t expect to attain your full earning potential using only a dedicated Twitter account. I think it’s essential for a keyholder to establish a Twitter presence (separate from your private account), but the most successful services also have a webpage. The best practice is to use Twitter to point to your own website.

Let’s face it. Twitter was designed from the start as a minimalist social media platform. All the character limits Twitter imposes on users throughout the site makes it impossible for the owner of a keyholding service to provide enough information to potential clients to generate much interest. However, with your own website, you have unlimited space to make your service stand out, which will attract more clients.

For a website, you will need a domain name, hosting plan, and a website. Web hosts like Bluehost, the one I use, have hosting plans starting at as little as $3.95 per month. On average, the cost of a domain name is around $15.

You can use WordPress, the most popular and fully functional content management system available to build, launch, and manage a beautiful website, and WordPress is absolutely free. WordPress allows users of all levels of expertise to quickly get a website up and running using drag and drop features. If you would rather not spend money on a website, many keyholding service providers use the free website building and hosting plan offered by a company called Wix.

The Learning Curve

While wearing a male chastity device is a rather straightforward proposition, being a keyholder is a responsibility. A caged client is not only putting his pleasure but also his safety into your hands.

Unless you already know a lot about male chastity, you owe it to potential clients to learn as much as you can about male chastity devices and some of the problems that can arise when a guy wears one before offering the service. Luckily, there is a lot of information on how to be a responsible keyholder available on the Internet.

There are also many books available on the topic written by experienced female keyholders. One of them, Ladies Introduction To Male Chastity, by Jules Scot, is available as an eBook on Amazon. You can read the book free if you’re a Kindle Unlimited subscriber. Also, I have a book on the subject, The Hitchhiker’s Guide To Male Chastity, that should be available in paperback by the time you read this, and that will be released in July as an eBook which will also be free to read by Kindle Unlimited subscribers.

How Much Can You Earn

As a small business owner, you can set your own rates. But, as a rule of thumb, most ladies who provide online keyholding services for between $40 and $50 per week. So, with only ten clients, you could expect to make $400 to $500 per week.

A few women charge less, and some charge more. The longer you operate a service and the more well known you become among male chastity device wearers, the higher the prices you can command.

How You Get Paid

Some online keyholders require payment in cash. Transactions can be conducted using PayPal or smartphone apps like Square Cash. Others accept payment only via digital gift cards, like those available from Amazon. All anyone needs to send you an Amazon gift card from nearly anywhere in the world is your email address. Some women accept cash or gift cards. They leave it up to their clients to choose how they pay. Obviously, as a service provider, you must require payment before providing your services.

Keep It Private

To maintain your privacy, choose a nom de guerre, a pseudonym, for your public presence on websites and social media. Many women use “Goddess” or “Mistress” in front of their assumed business name, which helps potential clients recognize the service you are offering. Also, create an email account to use specifically for your keyholding service for interactions with prospective clients.

How To Find Clients

Clients will find you by Googling search terms like “chastity keyholders” or “chastity keyholder service” if you have a website. They will also find you on social media platforms like Twitter if you maintain a social media presence. If you start a keyholding service or already have one, if you fill in the form on my contact page and let me know, I’ll be happy to list your service and contact details free right here on this site.

 

Online chastity keyholder services address a growing niche market. If you’re looking for a side gig to earn extra money, you might want to consider starting your own service.