The Chastity Training Manual

A Chastity Training Program for Males

By Mistress Cassandra


My name is Cassandra, Mistress Cassandra to you! I am a lifestyle Mistress and have developed this training program for males who need personalized lessons in service-oriented domination through enforced chastity. I know from firsthand experience that your motivation to delight me will soar as I artfully ration your sexual release. Your inborn, genetic craving for orgasms will be used to sculpt you into a spectacularly compliant servant. I find my boys derive pleasure from the profound physical and emotional experiences when anticipating an orgasm that is firmly under my control. I will be your guide on a journey to ever intensifying sensual highs propelled by your restrained sexual energy. If this sounds interesting to you, I command you to read on and to do so without touching yourself J.
There are many reasons boys choose to participating in my training. For example you may:
·         Want to try a chastity lifestyle before requesting it from your partner
·         Have a partner that has requested you to complete chastity training in order to better serve
·         Want to prepare for getting into the lifestyle and avoid “newbie” mistakes
·         Have a partner that has no interest in chastity and/or leading the relationship
·         Currently not have a partner and desire the thrills of relinquishing control
·         Need guidance in choosing, wearing and ultimately when to unlock a chastity device
Whatever your reason, I will provide the personal training you desire individualized to your specific circumstances. I have successful trained many, many boys to endure the aching of long-term orgasm denial. Whether you’re an unruly stud that needs to be broken, a powerful leader who longs to be a docile pet or a shy boy that needs a firm feminine hand to achieve satisfaction, I can supply the guidance you need. Ask yourself the following questions:
·         Does reading Female Domination stories, scenarios and scenes excite you? Would you like to try out one of these fantasies in a safe and secure environment with someone who understands and will indulge (and control) your fantasies?
·         Are you tired of impersonal computer programs and scripts whose instructions can be ignored and don’t respond to your ever-changing needs?
·         Do you need the personal touch of a strict but caring Mistress that will hold you accountable for your actions and misdeeds?
·         Have you fantasized about being wrapped around the finger of a beautiful woman and completely pussy-whipped?
If you answered yes to any one of these questions, you need to apply for my chastity-training program. In this program I will ensure that you experience both the realities of a chastity lifestyle and the powerful inspirational force that only a woman can exert as I toy with your desire. Just image how politely you will ask me for an orgasm after two weeks of denial. Will you be compliant to my whims and wishes? If I dangled sexual relief before your frustrated sex will you obey my orders? Will you beg me? Will you whimper if I reply “maybe tomorrow?” What will you promise me for the relief you so desperately need? If you want to answer these questions for yourself, apply for my unique chastity-training program. Remember boy, no touching yourself while you’re reading this J.

The Application

To apply for my chastity training, you must send me an application via an email with the subject line of “Chastity Training Application.” Note that all email addresses are discreetly handled and you will not be added to any mailing list without your express permission. In this application, you are required to describing yourself, your circumstances and any special requirements you want included or hard limits for your personalized training. Additionally, you are required to answer the following questionnaire that will be kept strictly confidential. Remember both honesty and attention to detail will be evaluated so take the time to impress me!
*Name or alias (this does not have to be your real name):
*How long have you been interested in chastity:
*Current relationship status (married, committed girlfriend, dating, other):
*If in a relationship, how will you manage a chastity program?
*Any female domination or chastity websites you frequently visit:
*Number of times you orgasm with a partner per month:
*Number of times you masturbate per month:
*What is the longest you have gone without an orgasm?
*On what date was your most recent orgasm and how was it achieved?
*Are you interested in assignments such as starting a blog, crossdressing, web tasks, or other?
*If so, state preferences and how much time per week you can devote to assignments.
(assignments are not necessary in the beginning. Chastity exploration is)
*How long do you want to be in chastity?
*Strict training or moderate?
*Do you like surprises should I decide you should be in chastity for a longer or lesser time?
*Do you own a chastity device?
*If so which one?
*Do you have a webcam available for training?
*Do you have any sex toys available for use under my direction? If so list them:
*Tell me about your kinky inclinations and if you want them integrated within the chastity program.
*Chastity is a commitment on both ends. You must do a weekly phone session while in the program. Sessions may be more frequent. A weekly session is mandatory. Regular e-mails with photo and newspaper are mandatory. Do you have the time to commit to this?
Once you have carefully and completely responded with all requested information, I will personally consider your application. You are instructed not to climax by any means until I respond. You are commanded to masturbate to the edge of a climax as many times as you are able only after you have sent me this application, but absolutely no orgasm! If I conditionally accept you, my response will give you instructions in preparation for the training program interview as well as my strict ground rules for the training. Good luck boy!

The Interview

At the mutually agreed upon time, you will phone me for your interview that will take 30 minutes or more depending on your performance and the circumstances. If you have a webcam, you will be required to show yourself (you are not required to show your face).  Here is an example of what you can expect during my interview call:
MC: Hello boy
you: Hello Mistress Cassandra, this is <name>.
MC: Are you prepared for your interview <name>?
you: Yes, Mistress Cassandra, everything is as you commanded.
MC: Good boy. Here are the rules for this interview.
MC: You will respond “Yes, Mistress Cassandra or No, Mistress Cassandra”
you: Yes, Mistress Cassandra.
MC: You will not touch yourself until I give you permission.
you: Yes, Mistress Cassandra.
MC: You will not climax unless I unambiguously say that you may.
you: Yes, Mistress Cassandra.
MC: Are you naked?
you: Yes, Mistress Cassandra.
MC: I didn’t instruct you to remove your clothes. Since you are new, I will overlook the infraction, this time.
you: Thank You, Mistress Cassandra.
MC: Get on your knees.
you: Yes, Mistress Cassandra.
MC: Place your hands behind your head.
you: Yes, Mistress Cassandra.
MC: Have you cum since you sent me your application?
you: No, Mistress Cassandra
MC: Good boy! Did you masturbated to the edge after you sent me your application?
you: Yes, Mistress Cassandra
MC: How many times boy?
you: Ten times, Mistress Cassandra
MC: Only 10 boy? You will need to do better than that to impress me.
you: I apologize Mistress Cassandra
MC: That’s better. Now lets have a little chat about your application, shall we?
you: Thank You, Mistress Cassandra.
. . .
The interview will progress as I probe your thoughts, test your responsiveness and judge your dedication. After all, my time is valuable and I don’t waste it on boys that are insincere in their desire for training. At the end of the interview, if you are lucky enough to be accepted, I will prescribe a program for you to follow for the remainder of the week. Continuation in the program will depend on how well you follow my instructions. 
Chastity Programs


Never done chastity but would like to try? This program is an intense cock control program with a cage. Many devices can be purchased from The Stockroom or from your local kink store. Any cock cage will do depending on your preference, you will hold the key and practice wearing it for Me. The usual choice of cock cage is one of the cb series. Boys love gadgets. This is why chastity is so popular.

The program is intense edging and then lockup for a period of time to get you used to Me controlling and owning the cock. You will start locking up for several hours a day, adding more and more time, sleeping in the cage, learning hygiene, daily emails, and a call with Me at least once a week for no less than 30 minutes.

During the lite program, a call of one hour with several Mistresses teasing you without orgasm will be expected on occasion. The last Mistress will be Me , playing with you and culminating in an orgasm or not. This depends on how you do with long term denial. On the lite program, it’s always baby steps. Find posts in the search box on this blog with “stroke pet alex” , and read about the stroking games involved.

A web cam is not demanded on the ultra lite program, but it is highly recommended if you are to move on to a more intensive program. Daily e-mails are demanded. A contract will not be necessary.

Plastic numbered locks are needed.


So youre ready for the cage to stay on 3-10 days, even longer? Plastic numbered locks and a spot check on the web cam when I decide is the program here. You must have your yahoo messenger on when home. I will inspect the numbers and the connection of the lock. I enjoy the convenience of numbered locks as they are very secure and disposable. No less than 1 call a week from 30 min to one hour is required.

Mostly I start a boy out for a 3 day lockup with daily photo of MY locked cock and daily emails. There is no stroking and edging during this lockdown. When the boy is let out of the cage, he will do as I say with tease and sometimes denial depending on our negotiation. Be reminded that I prefer a male in denial until I say he is no longer in denial. I may grant him release or I may edge him and lock him again. Personally I believe that boys who seek out a chastity mistress do not want to make the decision. It is all left to Me.


This being completely owned preferably with a permanent chastity cage such as a Lori’s device with piercing. The keys will need to be in your possession or use plastic numbered keys.  You will need a prostate milker such as an Aneros device because this program requires extended chastity. The longer in chastity you are, the more docile you become.

A Lori’s device is not the only device required but preferable . After all, chastity is a cooperative system and you must have a slave’s mindset. Only a device with a piercing is totally secure, and if you think about it, the key in your possession is a form of trust. Can you be trusted?

If you are ritual minded , a contract can be drafted. Chastity contracts are not bound by law. A contract can provide the sense of security of being owned by a Keyholder.

You will be available on i.m. during phone sessions, you will send daily e-mails with photo of MY locked cock, you will do tasks for Me. You can start a blog if you are talented in that or do some technical work, also artwork is perfect.  You will do no less than an hour call per week with cam.

Often I will share you with other Mistresses. 2-4 keyholder service is available.

Refer to chastity mistress for more information.

Yahoo messenger : yesmisscassandra


Blogs by MY boys: :

Acceptance and Defining the Curriculum

This section described the alternatives and questions the male must define for me in order to tailor the program to his specific needs and desires. At each level of the program, a commitment review may be initiated by myself in order to test/judge and correct the participant.  Consequences for unscheduled absences and unauthorized orgasms. Under construction.

Relinquishing Control – Level One

This section describes the initial regiment the male must follow. If he has a cage, it should be used. If he has no cage, a negotiation of what cage should be obtained and a schedule for doing so ensues. No uncaged males can enter level two. Under construction

Voluntary Confinement – Level Two

This section describes the chastity routine that must be practiced until it becomes habitual. Under construction

Extended Orgasmic Deprivation – Level Three

This section describes longer-term chastity periods must be successfully endured in order to prove dedication and worthiness. Under construction

Service with a Smile – Level Four

This section describes the training required to demonstrate the proper behavior, attitude and demeanor of a proper chastity slave for a female keyholder. Under construction

Anticipating the Request – Level Five

This section describes the actions the chastity slave must take to properly serve the woman. These include the ability to respond without provocation or request to both satisfy and delight his keyholder. Under construction