Best Chastity Letter Ever

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By Unknown

Rob:

You’ve long had a desire to explore Chastity, and although I’ve indulged you at times over the years, we’ve only played at the edges of your desires. That, Boy, is about to change.

I’ve carefully thought through how best to make sure you have the opportunity to explore your desires and explore a period of Chastity while keeping in mind that your fantasy may be more than you’d bargain for.

I’ve also considered our schedules, lifestyle and your high need for sexual release and believe I’ve found the perfect solution to meet your desires. This may not be what you’d choose if it were you making the decision, but the decision will not be yours.

I know you far better than you know yourself, and I understand that an exploration into your desires and fetish won’t work while we remain equal partners, so I’m making you my Chastity Boy. Understand that Boys don’t have cocks (those are for men); Boys don’t have erections; Boys can’t be trusted to stand and pee (you will sit to urinate); Boys don’t have pubes; Boys have chores with ramifications and/or punishment if they don’t perform them to my satisfaction; Boys don’t have orgasms.

I have no interest in your being a boy in any other area of our relationship, but until I decide otherwise, you will be a boy when it comes to your dick and exploring your chastity fantasy.

As my Chastity Boy:

You will be shaved from the neck down.. Chest, Ass, Crotch, Arms, Legs, Armpits will be completely smooth. You will shave yourself and present yourself for my inspection.

We will have sex one more time before you’re locked in the cock cage. Enjoy this sexual release, because it’s the last one I’m guaranteeing for awhile.

To ensure that this is a consensual agreement, you will beg and plead with me to lock up your cock as you’re approaching orgasm. You will beg me to take complete control of your cock and orgasms. You will beg me to make you my Chastity Boy.

Immediately upon achieving orgasm, the cock cage will be locked on your cock. I want it locked on while the last of your cum is dribbling out of your dick and before you even clean up.

The instant the lock snaps shut, you give up all control of your penis and orgasms to me. I will decide the next time you touch your penis as well as the next time you have an orgasm.

I demand the following as owner of your penis:

You will learn the benefits of chastity, the enjoyment of orgasm control and the pleasure of handing over all rights to your penis.

You will learn how to gain sexual fulfillment though bringing ME to orgasm and learn how your ass, mouth and other areas of your body can provide enjoyment despite not being able to cum.

You will not speak of your penis or your orgasms. The penis belongs to me, and you simply don’t have orgasms until I choose otherwise. When asked, you will respond with how MY penis is doing while locked in the cage.

You will learn to embrace your interest in chastity without complaint. You will not ask for release, or ask when you will be released. You will not like what happens if you complain or beg.

Since there are times when wearing the cock cage will cause undue discomfort or not be appropriate, I will allow it to be removed in the following conditions: Doctor Visits, Social Situations, Travelling or other situations as I deem appropriate. Unless otherwise instructed, you will not touch yourself or seek sexual gratification when out of the cage. On demand, you will put it back on and surrender the keys.

Your period of chastity will not impact my sexual needs. You will ensure that my sexual needs are met in any way that I choose. You will learn how satisfying it is to provide total pleasure to me without regard to your own sexual release.

Get used to this. I know you have a strong desire to be a chastised boy, but lack the initiative to do it on your own.

I WILL control your cock and you WILL become the boy you and I both know you want to be.”

Source: lockedguynyc

Effective Rule Making

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thegayboybible: 

“Boy, no matter where i place my dick, I expect you to ask permission before sucking it or fucking it. Beg me.”- Alexander Martin. I find rules incredibly hot. Being able to mold someone else’s behavior as I see fit to my own benefit is a big turn on. Below I’ll explore how to construct useful rules and the mindset to have while thinking them through.

- Lots of rules: Rules should help you craft the right headspace for your submissive. If you want him to feel like he’s in a highly disciplined environment you can certainly do that by creating a lot of rules. That requires you to create a lot of rules and remember them to enforce them. It also doesn’t allow for a submissive to enter subspace and just exist as a submissive because he needs to remain cognizant of rules. I, instead, advocate the use of fewer rules that are far stricter. For example: “Slave, before you may have food or drink, or make use of the facilities, you must first offer them to use at my leisure.” or “You must only wear clothing in public I approve.”

- Rules should have a purpose: This one sounds straightforward but you’d be surprised how easily making a rule purely for your amusement can be. Sometimes dominants can make up rules that are contradictory for the purpose of having an excuse to punish submissives. Submissives are logical people like anyone else and will know when you’re making shit up just to punishment. In this circumstance, it could simply be more productive to set aside time for punishment instead of waiting for your submissive to stumble into your clever pit trap. A submissive might fall for that once or twice, but thereafter probably wouldn’t once he recognizes the pitfall.

This brings us to the other side of that very coin. That submissives and dominants can absolutely get off on experiencing an enjoyment of pain through the lens of punishment. A submissive may feel a rush in being punished because he behaved badly and his Sir is correcting his naughty behavior. A dominant may enjoy the cat and mouse nature of a mischievous submissive that misbehaves and is caught who he gets to punish as he sees fit. From this perspective a rule is enhancing the enjoyment of dominant and submissive, bringing an erotic thrill to protocol.

- Rules must consider the submissive: I touched on this in the article I did about punishments. @bredbeta​ is a very obedient boy. He HATES to think he has displeased me in some way. My disappointment is for him a VERY severe punishment. If I were to actually punish him on top of that… he would be CRUSHED. I have a very different punishment and behavior corrective protocol for him than I would have for a boy who enjoys punishment (as described above). I do this because I know my boy. I consider who he is, and how I know him before punishing him at all. It is not unreasonable as a relationship is progressing to have a discussion about what punishments are acceptable. It is true, it certainly does impede on the fantasy made reality a bit to get submissive approved punishments, but would you rather punish someone as you see fit and potentially have him leave you and never come back or would you rather retain that submissive? You could be someone’s story or worse yet, someone’s bad experience he flashes back to when trying to trust other dominants. Take the time, have the conversation. Listen.

- Rules should be based on what’s realistically possible: This is the difference between having a submissive in chastity and codifying a rule that he must submit a photo of his locked cock once every 5 minutes to your phone via text message, and a photo once a week every week when he’s away from town. I am a big advocate that in being honest about who we are as dominants and submissives alike that we can indeed create relationships that account for our flaws. For example issues around cheating (as discussed in the relationships article). I would even go so far as to suggest that rules when initially created be acknowledged as transitional until you can try them out and see how they fit for both parties, then tweaked when and where necessary. As dominants we are responsible for our submissives and their wellbeing. That is a power we must all endeavor to take seriously.

Creative Chastity

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Alexander Martin:

I have had some mixed results with locking up a boy’s cock in a cage. For some, their cocks had been too large to comfortably fit into the cage. Some boys tried it and found metal and plastic cages just too uncomfortable. For one boy, he figured out that he could actually slip out of it at any time.

Having a lot of those troublesome experiences has lead me to the conclusion that there are people who just find the idea hot but it loses its luster in the execution. Conversely, the chastity players who have really found meaning in it, for whom it’s become a daily part of their life whether or not a Sir is their keyholder, find ways to make it work. And that is the key. Find how to make chastity work for you and understand and accept that your chastity play may not look exactly like what’s on tumblr, but is valid nonetheless if it gives you what you want to get out of the experience.

I write this article for readers who are interested in chastity but are having some difficulty with the standard lock and key. When the standard approach gets difficult, it’s time to get creative to find a way to make chastity play work for you!

- Shorter goals: The first adaptation to chastity play to make your goals more doable is simply to make the locked periods shorter. The denial makes the eventual orgasm sweeter anyways. You will see many players online bragging about the length of time they can stay locked. If that’s what gets them off more power to them, but if you just want to experience some denial for awhile and enjoy having sexual feelings enhanced due to the horny build up of not orgasming… then does it really matter if you’re locked till the weekend or till 2050? Hell, you may even eventually find a sweet spot where you stay locked up (for example) for 3 months at a time and that’s what works best for you. Your dominant might tease “Oh man, 2 more weeks till you’re out boy. It’s been a long 2.5 months so far. Remember when we watched porn each night for a week before bed? Good times.” If shorter goals are enjoyable and you get the experience out of it you want, DO WHAT WORKS.

- Key willpower: When the length of the goal isn’t an issue, often willpower is the big obstacle. Being so horny makes it hard to make the decision to stay locked. Where willpower is an issue dominants are often not involved in a chastity player’s life. The purpose of sealing away the key is to provide an obstacle which while not insurmountable gives you sufficient pause to reassert your willpower. There are two pretty reliable options:

Envelope: Put the key in an envelope, seal it, give it to a friend, and tell them to give it back to you in a week. If they ask about it you can make something up if you like. One of the favorite stories a submissive told his buddy was that he’d put a credit card in there he wanted to not be tempted to use until date X. His friend was more than happy to hold onto the key to the box with his credit card in it without ever realizing what the key actually unlocked.

Timed safe: This sounds like a much more expensive option than it is. One of the safes that have been making the rounds lately is a safe for kitchen use to help control temptations. I’ll include a link at the end of this section. You can just toss the key inside and set a time limit. The safes are about $55 so they’re not impossible to save for, but they’re also expensive enough for you to probably think twice before shattering it to get the key.

- Comfort: The holy trainer and metal cages are the two most comfortable cage types. If you are interested in a holy trainer, please consider that first off there will be some international shipping involved which is unsurprisingly expensive. Additionally, I the official website DOES NOT accept opened products for return. Be certain you get the right size before you order it. In light of that, I strongly suggest you take a trip to a sex store in your city or a local kinkster event and get fitted for a cage the first time you get one. You may have more options there in terms of what you can buy a sales person who can give advice, and the opportunity to talk about how active you’ll be in it, or some of the issues with comfort you’ve had. Lastly, if you aren’t already aware, chastity cages are generally most comfortable when you have little to no hair while wearing them as it reduces the likelihood of getting pinched or having hair pulled.

- Sir’s orders: When Sirs are involved with chastity play, you can have a Sir leave you unlocked but absolutely forbid access to your own genitals without his supervision. I have been surprised how well this works for some people. They simply needed to be told no and that was all it took.

- My grip: When a dominant is in charge of orgasms, you may also find that Sir will do the masturbation for you. When I’ve offered this choice, I restrain the submissive’s hands (and in some cases legs) add a little baby oil, and stroke until they cum and then just keep going. They can orgasm in exchange for continuing to be stroked after orgasm. If I’m feeling generous, I’ll offer them mercy in exchange for something later on of my choosing. It should be of no surprise to anyone that mercy is almost never worth it later on but it still gets chosen fairly often.

Milking

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Alexander Martin:

Thanks to reader @flashdoggy for a topic suggestion.

Milking is the act of taking one’s boycock and stimulating him to completion. As always it is important to have a reason for your actions in mind. Is milking a load from your boy a reward for faithfully following your will in staying chaste? Is this a punishment for a chaste boy who did not do his chores for the 3rd week in a row?

Reasons to Milk

- Chastity: Chastity interacts with milking through the obvious denial and later release. If you really want to know a ton about the interaction between chastity and milking you should be following @chirenon. He’s probably the most prolific poster of male chastity on tumblr (he does occasionally post mmf too, so if you’re squeamish be aware). Regardless, some folks believe that a chaste boy needs to be milked for health reasons, others say that’s bullshit. I cannot definitively find an answer (that seems reliable) either way.

- Reward: Milking is a reward usually for boys who cannot or do not desire long term chastity. It’s a reward that they wait for however long they’re locked away, and when they have waited for quite some time for orgasm. Outside of chastity, some submissives take it as a sign of submission to give up control of pleasure to their dominant. In this way a dominant

- Punishment: Chaste men often take great pride in the length of time they’ve managed to stay chaste. If one misbehaves, you can threaten to milk him if he does not shape up. Fair warning though, if your chaste boy takes his chastity very seriously, it would be considered a very serious punishment and if the punishment doesn’t fit the crime you could do damage to your relationship. Alternatively for submissives that are not chaste the punishment side of a milking is when you choose not to stop milking when the orgasm occurs.

Ways to Milk

- Masturbation: A hand with or without lube is standard. If you’re lucky enough to own a stroking toy such as a flesh jack or a gel sleeve those are also fine options. It’s worth knowing what region of the boycock is most sensitive. Sometimes rubbing the head will be all that’s necessary for orgasm. Other times the frenulum (look it up) is the most sensitive spot. The last area that can be worth exploration is the Penile Raphe. It’s the urethral tube that can be seen running along the underside of the penis. Rubbing it in circles, lifting it from the penis and rubbing it between two fingers can be ways of stimulating the raphe.

- Tease and Denial: Better known as edging. Simply put you make a big effort to get your boy as close to orgasm as possible and stop. I do not suggest brinkmanship while edging. I have seen and heard of this mistake a lot. Your objective is to get him close and then back off. Do this over the course of an hour and he’ll be begging you for orgasm. Of course whether he’s earned such a reward or punishment is up to you…

- Over-stimulation: He’s panting, his face is red, and he’s so close he’ll blow his load any second now. You ramp up the intensity and he boils over jizz squirting everywhere, only you don’t back off. You maintain that intensity. He begins to writhe, to squeal, it’s too intense. That is over-stimulation. I’ve mentioned it before in other entries, but I often couple this with tease and denial. It also works well when you present a boy a deal with the devil. You’ll stop your over-stimulation in exchange for a particular task or activity that benefits you. Get creative.

Advice For A Boy During His First Locktober

Hello Sir, I love your blog! I was just wondering if you had any advice for a boy during his first Locktober?

Alexander Martin:

Hi Beta!

Uh, since this is your first Locktober I’ll keep my advice pretty generic and hope some of it is new to you.

Remove the hair - One of the most aggravating things about chastity is that the hair gets caught in the cage as you walk. This can result in pulling a hair out of your skin and sometimes cages even pinch skin as well. However, we can control the amount of hair for it to get caught in so remove it, whether that means shaving (if skin irritation as a result of shaving isn’t an issue for you) or waxing (on your crotch you might be able to do this alone, but it’s best to have a friend or lover assist). If you’re going to wax your cock, be sure to look up all the info you can online about how to wax safely. After all, your scrotum is a very thin layer of skin, there is no fat or muscle to protect your testicles so be VERY conscious of pouring hot wax onto it.

Keep clean - It is OK and appropriate to let it out periodically (once a week, or once every two weeks). Chastity cages can make it very difficult to get the skin cleaned up. Clean it up, towel it off, and put it away when you’re ready.

You can lend the key to a trusted friend - If you’re in need of someone else to hold onto it. You CAN lend it to a friend you trust to keep it safe without telling them what it is or what it’s for. Do make sure they’re organized because when Locktober is over, you… obviously need that key back… Or a pair of (small) bolt cutters and a new lock and key.

Chastity isn’t about how long you can go - Chastity is about finding the most sexually interesting and satisfying way to enjoy chastity. Some men find that when they’re constantly horny and locked they feel both secure and focused. They feel more ready and able to meet the demands of their Men at a moment’s notice. There are also guys who put a cage on for say… three months then take it off on a Friday and jack off all weekend coating their homes in jizz from their overfull balls. Whatever method works for you is the right way to do chastity.

If you can, share the secret with someone else - The most fun you can have is having it as a dirty little secret with a lover or FWB. Someone who can engage in that smile, wink, and nod with you when you’re out to brunch. Someone who can tease you mercilessly knowing there’s nothing you can do about it. Use Locktober to become closer with another person.

The entire purpose of Locktober as I understand it is to give people interested in trying chastity a reason, an excuse, and a time frame to try it out and see to what extent it works for them. Even if you find chastity isn’t for you that knowledge is as valuable as what IS for you. If you end Locktober and are beating yourself up for how you did? That’s how you do Locktober wrong.

Thanks for the question, and I hope you have a fun and frustrating month!!

Male Chastity? What's the Point?

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Anonymous asked : I don’t understand the point of locking up. What does this do? Why is this attractive? Not trying to judge but trying to understand why the gusto for “caging” a dick.

The Silent Alpha

Fair question.

Everyone can love chastity for different reasons, of course, just like any other kink. Here’s why I do:

Chastity takes away a boy’s ability to use his dick. He can’t jerk off, he can’t penetrate anything, he can’t stimulate it, he can’t get hard. To me (and to a lot of people) the dick is the ultimate symbol of masculinity. So when a boy doesn’t have access to it the feel of masculinity alters. He’s no longer in control of his dick, it is now controlled by the keyholder. The boy doesn’t get pleasure from it, the boy can’t get hard, depending on the device, the boy might not even be able to see it. It’s emasculating.

Not being able to cum makes the boy very horny. You’d be surprised what males are ready/want to do after not being able to cum for a few days/weeks. That makes him look for pleasure in other places. He wants to be touched anywhere, he wants to touch. In gay boys’ cases they think about dick non stop. They start playing with their ass to get some release so their hole becomes their sex organ. And because their hole is being stimulated and they get pleasure from it, it’s not just a hole anymore. It’s a cunt. They may not want to call it that, but that’s what it is in their head. So we now got a boy who’s hungry all the time, he trembles from the slightest touch and gets lots of pleasure from his new sex organ.

Chastity improves sex for the boy. Not only is he more sensitive, but without being able to cum he will always enjoy sex. If you bottom, you know that if you cum - it’s game over. Your top has to stop because you don’t enjoy being fucked anymore. That problem goes away with chastity. Boy is always ready and eager. That, of course, makes sex better for me. Not to mention the hands free orgasm the boy can achieve after enough time in chastity. Once a boy cums without stimulating his clit, he’s changed forever. 

Chastity also never lets a boy forget who he is.You may be a bottom, you may be a sub. But you don’t think about that part of you when you’re at work or visiting you family or going to parties with your friends. The chastity device is always there, you can always feel it. Horny or not, sad or happy, alone or surrounded by people. You can always feel it, it’s a constant reminder that your manhood was taken away. It keeps you in your place, it never lets you forget that you get pleasure from getting fucked. Every time you need to use the bathroom you are faced with the reality of who you are : male but not a man. That changes a boy. His behavior becomes that of a sub even outside of the bedroom.
Chastity builds up a lot of frustration and tension. That’s why it’s also a great way to motivate the boy go to the gym or be more productive in general. I’ve had a boy with a barely average body transform into a beast after just 1 year of chastity. I’m no longer his keyholder, but he still keeps the cage. He doesn’t want it off, because it motivates him so much.

And most importantly, I love chastity because it sets clear roles. The boy is giving up his masculinity for me, he locks it up as a sign of surrender. My dick becomes the only dick in the room and he’s just holes. I’m his Man, he’s my bitch. Fucking a boy while watching his soft clit in his cage being ignored is just very, very hot. 

I never liked when my bottoms touched themselves during sex. I thought the chastity devices looked a little weird at first. But now I love them. If I see one on a boy it makes me hard instantly. Because that means that he embraced his role as someone who belongs underneath Men. And I love being on top!

Chastity Play

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Good evening Sir i am a total sub that has a huge chastity fetish and have been in search of a DOM key holder but have not had a lot of luck. So my question is do Doms like sub fags in chastity or will i just have be self locked up. Thank you for your time Sir

Papa Tony:

I wish you great success in your search. Perhaps my own experience will give you some ideas:

My slave met me when he was 52, eight years ago. We originally started out at Daddy and boy, but he gently worked on me as time went by. He’d encourage me to try put new kinks with him, and he made it very rewarding indeed.

As it turns out, we found great success with chastity play, and it continues to this day. He provided three cock-cages (and has strong opinions about each of them). I keep the key to his favorite in my desk drawer. I decide when the new phase begins, and I decide when it ends.

I issued Standard Chastity Orders years ago, and he continues to follow them, once the lock clicks:

- When he is caged, he has to perform prostate maintenance by wearing a specific butt-plug for a minimum of an hour every day. Ideally, while he is actively moving around. What makes THAT butt-plug so important? Because it is the exact size and shape to apply maximum stimulation to his prostate.

- He is to issue a report via text-message every evening. I read every one of them with great interest, even though I may not always reply.

- When under chastity, he will perform chores for me while I keep an eye on him, wearing nothing but my collar, a butt-plug and a cock-cage. This sight excites me. It is highly symbolic of the relationship that we share.

While he is under chastity, his IQ drops. 😀 He gets so desperately horny that his submission intensifies. His service to me becomes everything in his life.

I make sure that the latest time under chastity ends with a mind-blowing orgasm. This is my choice.

I don’t consider a single part of this kinky pleasure as a chore, or an obligation. I have found that it suits my desires as a Dominant.  Chastity play (for THAT submissive) is not my second choice. It is my FIRST choice.

I wish all of this for you, brother - Don’t give up!

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mastera6 says:

It can be hard to find a key holder and even harder to find a Master/Dom who understands it fully. They are out there but it can come down to right place/right time type of situation. It can also be discouraging when you can't find someone so it's best to take a break if the search becomes overwhelming.

Being self locked is a great start because you have learned how to function in the device and when you come across the right man you can give your keys without fear.

There are sites such as www.lockedmen.net where it's chastity based which can increase your chances. The main thing is to be patient and persevere and keep in mind that you want a good one and not just a convenient one. Do not let desperation let you make a bad choice.