my lessons in tease, orgasm denial and Femdom control training


Continuing education with Mistress Cassandra

Yesterday I was permitted to talk with my wonderfully imaginative Mistress Cassandra. Having been two weeks since my last orgasm, I was very, very anxious to be allowed the privilege of just touching my cock in a stimulating fashion. Knowing this, Mistress cleverly had me prepare by ordering nipple clamps, prostate massager and the electo cock strap to be applied before contemplating any masturbation. Finally, after what seemed an eternity with the clamps  biting, the massager vibrating and the electro energetically pulsing, permission to touch my cock granted. I reveled in the glorious relief so long forbidden. The orgasm I so hungrily craved quickly approached. I stayed hovering on the edge, enjoying the sensations that I knew would be all to brief, while my Mistress enjoyed the show.  After seemingly only minutes (I’m sure it was longer), I was ordered to lock myself back into the cage without orgasm. Thus motivated I was given two assignments. First, the posture collar was to be locked around my neck until such time as she chose to release me. The second task, which was far more challenging, was to identify areas in which my service to both Mistress Cassandra as well as the Head Mistress needed improvement. Sleep did not come easily that night. Thinking about what to write while locked in collar and cage had me whimpering in frustration. I mailed my self-revealing letter to Mistress Cassandra this morning. What will she decide my next lesson should be?

Two Watchful Mistresses

It was a weekend of mind numbing, bone jarring, raw hot sex that was worth every agonizing second of the month long denial which preceded it.  Now, however, my beautiful Mistress Cassandra has ordered me back into the cage for another sentence of indefinite chastity and denial. I don’t know what she has planned; I only know that I must obey. My cock is now confined in the unyielding grip of pure surgical stainless steel, The Watchful Mistress by Mature Metal (you can see the evolution on my Mistress Cassandra’s blog). My first night in this new chastity device was sensuously maddening. While comfortable to wear, its custom fitted confines allowed no room for expansion of any sort. The hardened metal quickly dismissed any hints of rising passion as easily as Mistress Cassandra does in our all too infrequent encounters. So I begin the long wait again… my desire mounting as the hours pass. I know from past trials that I will soon become desperate for relief. Frantic with cravings that will be exploited by my cleverly cruel yet hauntingly desirable Mistress; I will succumb to her rule. The future is not yet written.

A Month of Denial and the Head Mistress

Last night, after 31 long days and nights of chastity, Mistress Cassandra allowed me out of the cage. Orgasm, however, is strictly prohibited until my wife (or as Mistress Cassandra calls her ‘The Head Mistress’) grants me that favor. Until then, I am permitted to masturbate and edge as much as I desire so long as I defer control of my first orgasm in over a month to the Head Mistress. The waiting is excruciating torment. My goal so close yet still out of reach. Waiting for a woman to allow me the pleasure my body so desperately craves. Mistress Cassandra’s voice is still ringing in my ears, “only she can relieve your aching desire”. So I wait…

Mistress Cassandra, Queen of Denial

Last weekend, in addition to being permitted “free range” status, I was also given several assignments by my provocative Mistress Cassandra. One of these was to edge every hour when I wasn’t sleeping. The manner in which these edges were to be performed was rigidly prescribed; naked, on my knees before her image and chanting “Mistress Cassandra owns my cock”. Additionally, I was to prepare an image of my beautiful Mistress as Cleopatra, Queen of the Nile (or is that Queen of Denial). So between the hourly alarms signaling my obligated self frustration, I assembled the required artwork and pieced together the scene in Photoshop. Tracing the curves of her luscious body to blend the images together to meet her demanding quality standards was pure torture. My desire to release, built over weeks of enforced chastity, spurred my desire to achieve perfection in my task. As the hours passed, the image took shape in a way that I hoped would please her. Striving to impress (like all males in chastity must), I also created an anaglyph; a 3D version of the image that appears when wearing red/cyan colored glasses. As the weekend came to a close, and after 34 edges delivered with the proper reverence, I sent the final image for Mistress’ inspection. My reward for this obedience and creativity… stay tuned. You can see the final product and read the story that inspired it on Mistress Cassandra’s blog.

A Gift from Mistress Cassandra

Collared for Mistress Cassandra

This past weekend, after eleven days locked in chastity, Mistress Cassandra favored me with her attention. First, thankfully, I was released from my chastity cage. Just being free from its confining grasp was gift enough to have me profusely thanking my imaginative Mistress. I slowly, deliberately, caressed the flesh that been denied for so long. However, manual relief was not what Mistress had planned for me. I was commanded to strap my cock into the electro harness for her entertainment. Slowly she forced the dial up, up and then up again. “More Juice” she demanded with a haunting chuckle.  I complied until my whole groin was buzzing with the electrical torment. Still not satisfied she required nipple clamps to further my submission. I complied, as always, to her directives wanting nothing more than to release my desire which she had so cleverly cultivated over the preceding days. Thus, judging me now properly conditioned and motivated… we talked. She comfortably seated while I stood clamped and highly charged. We discussed service-oriented submission as described by Ms Rika. It is not what the dominant does to the submissive but rather what the submissive does for the dominant. With the electrons sharply kissing my cock, her words made so much sense. I could do nothing but agreed with her irrefutable logic. Then, with Her lesson properly taught to her captive student, Mistress Cassandra instructed me to lock myself into the cage once again. There would be no orgasm today. Finally, since I had followed her instructions so dutifully, my kind Mistress gave me a gift. A gift that would last me the whole weekend. Under her careful supervision I was requested to lock a posture collar around my neck and fasten it with a numbered plastic lock. I quickly compiled and found myself standing at attention under her gaze. In a voice that I could tell was delivered with a smile, my sweet Mistress informed me that I could remove the cruel collar on Monday morning… but she might check back beforehand to insure strict compliance with instructions. So for the remainder of the weekend I stayed doubly locked for my beautiful Mistress. Thank you for my gift.

Humbler, Holiday Submission and Returning to Chastity with Mistress Cassandra

On the day before I returned to my wife, Mistress Cassandra gifted me with an erotic session I will never forget; an hour locked in the humbler. With this cruel device locked around my balls, Mistress instructed me to parade back and forth on my hands and knees while she observed my plight via webcam. Being locked in such a manner while reading Mistress’ instant message “this is all for my amusement” invoked shivers of desire. All I could do as the seconds ticked slowly past with the persistent tug on my balls was to look lustfully at the image of her seated comfortably gazing down at me. Talk about a submissive experience. Even when the hour had elapsed, Mistress was not finished with me. I was treated to an hour of hardcore tease and denial that left me breathless. Finally, still not satisfied, Mistress instructed me to edge every hour until I met my vanilla wife. Thus prepared by my devilishly clever Mistress, I was incredibly aroused and ready for sex with my wife when the moment thankfully arrived. I got on my knees next to her and licked pussy slowly using techniques I studied and practiced. She responded fervently, saying that her orgasm snuck up and overwhelmed her. My release was, needless to say after 23 days of teasing, overpowering. I went to sleep satisfied for the first night in a long time.

Holiday Submission

During the holidays, I followed Mistress Cassandra’s instructions precisely. There was neither stroking nor any solo orgasms. The only relief I received was what my wife granted me. Following Mistress Cassandra’s and Ms Rika’s teachings, I performed unrequested tasks that would hopefully endear me to her. Lots of neck, back, leg and foot rubs in the morning, evening and periodically in between. I would wash dishes in the morning when I found them. I made the bed after she came downstairs in the morning. I worked a few big projects around the house that she had been waiting for. All of these tasks were done without the expectation of reward. However, the results included some spectacular love making, albeit not as often as my desire. Nonetheless, it kept me motivated to perform many “special” duties to make the holidays enjoyable and memorable for her.

Returning to Chastity

Upon returning to Mistress Cassandra’s control, I dutifully reported my progress, development and status. I also humbly requested one more orgasm before going into chastity for an indefinite period. After considering it (and keeping me in suspense) for a day, my Mistress granted my request… and more. She rolled the dice and announced, to my astonishment, that I would be required to have not one orgasm but four in the next hour. On my knees, I enthusiastically reached the first in record time. After a short break, Mistress’ commands in my ears goading me on, I was just barely able to follow her directions and spasm a second time. After that, however, no amount of coaxing could get me to the third so I unfortunately failed my Mistress (an act which I am sure I will have to pay for in the future). So here I am, locked again and at her mercy. I’m sure I will look longingly back at those missed opportunities to release with regret. I thank my wonderful Mistress Cassandra for all the time and effort she puts into my training. I am a better man… well, she would have me say boy for it.

Mistress Cassandra’s City of Chastity and Denial

Mistress Cassandra's City

Cassandraville – Where all your wishes don’t come true

For those of you that have anaglyph (red/cyan) 3D glasses, click here.
Alternatively, if you have anaglyph (blue/yellow) 3D glasses, click here.

Ballad for Chastity Mistress Cassandra: 50 Ways to Lock Your Lover

(you know the tune)

The problem is all about your cock
She said to me
The answer is easy if I
Lock you with this key
I’d like to make that penis struggle
To be free
There must be fifty ways
To lock your lover

She said you’ll really lose that habit
To protrude
Furthermore, I hope my key ring
Isn’t lost or you’ll be screwed
But I’ll repeat myself
While you stand there in the nude
The must be fifty ways
To lock your lover
Fifty ways to lock your lover

Don’t slip out the back, Jack
Get a new lock, cock
You don’t need to be stiff, Biff
No way to get free
Hop in the truss, Gus
No room to get hard much
Just drop off the key, Lee
And sit down to pee

A Vanilla Wife, a Gifted Mistress and me

If you’ve read Mistress Cassandra’s blog, then you already know my somewhat unique situation. However, since many who happen upon this site have not had the reward of perusing her writings, I will describe it again here. Business requires me to spend much of my time in Silicon Valley. This creates a personal challenge since over the course of many, many years I built a life and raised children with my wife on the east coast. Being absent from my eastern home for 2 to 4 weeks at a time definitely has its downsides, but surprisingly, introduces a few benefits as well. My wife and I both actively work to enjoy our limited time together and that avoids the staleness normally accompanying an endless routine.

Finding Mistress Cassandra

Having a lifelong unfulfilled fetish for Femdom, I would occasionally surf the web for sites that feed this desire when the need arose. Earlier this year, I came across Mistress Cassandra’s site and something just clicked. I later described the effect to Mistress as “haunting”. Over the course of several weeks, I returned again and again; reading the details of how she expertly dominated and controlled men from afar. So, uncharacteristic for me, I called and talked to this talented Mistress of chastity. Intuitively she understood my wants, needs and desires and kindly accepted me as a slave-in-training for Femdom orgasm management exclusively by her when I was located on the west coast. Thus, my days (and long nights) of instruction began as I became her chastity slave.

Chastity Training in Baby Steps

Mistress began slowly, baby steps as she would say, to modify my daily activities into that of a good submissive. I was required to purchase a cocklock and submit to random chastity inspections via webcam. Orgasms were, of course, forbidden except by my Mistress’ explicit permission. The effect of all this was intoxicating. After years of fantasies, I now had a real dominatrix controlling and directing the most intimate details of my sexuality. Of course I probably could have cheated in this chastity training, but I vowed never to do that. For some reason (Mistress says it is because I’m a true submissive) it was important for me to earn her praise and approval. She was, and still is, strict. In those early days of my training I had not been granted the privilege of see her instant messaging status and thus had to be ready for her direction at all times. I worked hard to meet or exceed all of her rules and requirements. Interestingly, the rewards, and occasional punishment, Mistress Cassandra favored me with motivated me in unexpected ways. It went beyond just trying to earn the all too infrequent sexual release, I truly wanted to please and pamper her.

Mistress Cassandra’s Slave-In-Absentia

My motivations changed, I set to the task of being a joy in her life. By this I mean it was no longer about what she would do to me, it was all about what I could do for her. I tried to anticipate requests, create thought-provoking messages on topics that interested her and generally find ways to make her life better. For these efforts, I was rewarded with the status of slave-in-absentia, someone who could perform daily activities, albeit remotely, that would enrich her life. So, to this day I continue to look for ways to please my wonderful Mistress. She gives me assignments, like this blog, and I carry out those instructions to the best of my abilities and in a manner that hopefully reflects both my appreciation and devotion to her. I am proud to call her my Mistress and will do what I can to achieve my coveted reward… hearing her say “good boy”.

Essential Reading for Male Chastity Slaves and their Femdom Mistress Keyholders

The quintessential guides to Female Domination

Female Domination – Elise Sutton
The Femdom Experience – Elise Sutton
Worshiping Your Wife – Mark Remond
Uniquely Rika – Ms Rika

Understanding the Male Chastity Experience

Male Chastity: A Guide for Keyholders – Lucy Fairbourne
Be Careful What You Wish For… The Ultimate Guide to Male Chastity – Sarah Jameson
Everything you wanted to know about male chastity, but were afraid to ask. These ladies are experts in the science of harnessing the male potential.

The Tongue is Mightier than the Sword

Oral Sex She’ll Never Forget: 50 Positions and Techniques That Will… – Sonia Borg Ph.D.
She Comes First: The Thinking Man’s Guide to Pleasuring a Woman – Ian Kerner
How can you pleasure your mistress when your cocklocked? Reading to improve your oral knowledge and technique. Remember, Mistress comes first!

Classic Fiction that Defined the Genre

The Woman of the House – G. F. Green
A once traditional marriage evolves into a remarkable Dominant/submissive relationship, as Pricilla becomes Goddess to her submissive husband, and trains him to serve her every need-from free man, to slave for life, contract-bound to please. A delightful primer on the virtues and rewards of a Female-in-power relationships.

The Yes Man – G. F. Green
Read of a young man’s journey into enslavement to a naturally superior woman.

Debbie’s Gift – Amity Harris
The classic internet story of high-tech male chastity and Femdom male management. Soon to be brought to life by DreamLover Labs?

Jessica – The Mule
What would a collection of female domination stories be without one where a secretary dominates her boss?

Making of a Mistress – The Mule
Is a dominatrix born or made? Link points to a text file containing the introduction. Additional chapters are in the same location.

Essential Audio Links

Hot audios recorded by Mistress Cassandra in her oh so sexy, teasing and sultry voice. A must listen for all male chastity enthusiasts.
Mistress Cassandra
The Chastity Show
Tease and Torment
Chastity Mistress

An open letter to Mistress Cassandra

To the wonderful woman I have the honor to call my Mistress!

It was so very enjoyable to talk and play with You last night. I was tired from the day’s work but You weaved your magic, as You always do, to drive me to intense levels of frustration with no other thought than to hear you grant permission for orgasm. All the day’s worries melted away and all that was left was pure, unbridled passion. The parachute action was intense; I still feel its erotic ache this morning. The prostate massage was delicious; goading me on to higher levels of desire. The nipple clamps were cruel yet motivating. The electro, especially where you had me attach, was forceful and fervent. Completing my attire with the posture collar, a technique that forced me to look directly at Your lovely features, was truly inspired. Then when You had me properly harnessed, impaled, clamped and charged, You played with my lust like a cat plays with its prey. On and on it went with time standing still. I was the violin and You were the virtuoso performer. You kept playing and the music was so sweet and passionate. You kept me hoping, begging, praying for release for so, so long. But alas, in the end You denied me and so the night passed slowly, my lust still fueled by Your sexy voice echoing in my brain. It is only your continuous conditioning which prevents me from putting out the fire You ignited. I surrender to Your supervision and will follow Your instructions as dictated. Thank You, my exquisite Mistress Cassandra.

With admiration and affection,

Tease and Denial, Mistress Cassandra Style

When I have been good, Mistress Cassandra will allow me to go free-range (an amusing euphemism for being uncaged) for a short time. This gift is usually granted after being locked continuously for at least a week. The feeling of freedom is heavenly after these long periods of restraint and I attempt to savor each moment that is allowed. When my creative Mistress does finally permit release from the cocklock, it is accompanied by its own unique torments; specifically tease and denial. She has developed many deliciously cruel techniques to intensify my already acute frustration during this time. I never know which training method She will impose, but I accept my fate as a good chastity slave must.

Tease of Damocles

This method of teasing is insidious in its elegance. Through some random mechanism, or occasionally just at Her whim, Mistress determines the length of time I will remain uncaged but keeps this information a secret. The duration may be as short as 15 minutes or as long as 24 hours. During this interval I am permitted as much recreational stimulation as I desire, without orgasm of course. A touch, any touch, so long denied feels exquisite. With my body craving the satisfaction, I indulge. Since Mistress’s instant message declaring playtime is over can arrive at any moment, the drive to take advantage of my unlocked condition spurs me to ever greater levels self induced frustration. When the time finally expires and Her message appears, I reluctantly lock the CB-6000 back on my unrelieved member for another indeterminate term of imprisonment.

Free Style Tease

When given this assignment, I am required to stimulate myself to the edge of orgasm a fixed number of times as specified by my demanding Mistress. Additionally, I may be given restrictions or requirements to compound the effect of the tease. For example, some of Her favorites are to required that each edge be separated by a complete loss of erection or that the edges be no closer together than 15 minutes. On some occasions the edges are required on the hour and instant messages must be sent to confirm compliance with the possibility of on camera inspection. At the end of this mission, I must write a report detailing when each edge was performed and what I was thinking during each excruciating event.

Femdom Fiction Tease

Mistress Cassandra requires that I keep Her informed of new works in the Femdom and chastity genres. To this end, I may be required to read and review new literature during my cocklock hiatus. (Reading erotic Femdom fiction while locked is a punishment I desperately try to avoid.) I am either given a novel by Mistress or recommend one for Her approval and then am assigned the tasks of reading and submitting my review of the book along with any original techniques or unique scenarios presented. Since books on these topics tend to inflame my already tortured libido, I spend much of my allotted free range time rampant and unrelieved. I’m sure this is my Mistress’s devilish intent. I am sometimes quizzed on enslavement techniques and Femdom orgasm management so I must study the prescribed manuscript in agonizing detail.

What is a good chastity slave?

The first rule for a chastity slave is to always remain chaste for his Mistress. This means NO CHEATING… EVER. Adherence to this rule is paramount. If you are lucky enough, as I am, to have a Mistress that cares sufficiently to cocklock and dominate you, don’t ruin it by cheating. You will feel guilty. You will fail to perform to expectations. Worst of all, you disrespect Her by cheating and no lasting bond can survive that. Rather than cheating, channel all those desires into productive actions that will please your Mistress. Activities such as cleaning the house for Mistress, composing your Mistress a song or writing Mistress a blog are examples of converting all that pent up sexual energy into positive and useful tasks. I heartily recommend this approach because it increases satisfaction ;-) for both you and your Mistress. The second rule is total obedience; always carry out the commands and desires of your Mistress in a timely manner to the best of your ability. A lazy or insubordinate slave will soon be dismissed by any sensible Mistress. So, if you want Her to keep you around, take pride in your duties and complete them with distinction. Always remember that obedience is rewarded :-) while disobedience is punished.

Obeying these first two rules will make you a chastity slave, but how to be good chastity slave? Always be a joy for your Mistress. You should be the least stressful, lowest maintenance thing in Her life. Do everything you can to make Her happy and looking forward to your next encounter. You should listen carefully to determine what brings Her pleasure. Be caring and attentive to Her needs and desires. Surprise Her with occasional gifts that demonstrate your responsiveness to Her wishes. Don’t whine about being locked. An occasional quip, delivered humorously, about the condition of Her cock should fetch a smile, but don’t be tedious. Don’t be sullen when you’re not released. That’s completely under Her control and discretion. Rather, accept it and strive even harder (pun intended) to earn the gift of free-range, at least for a while. Be creative. Going above and beyond Her basic requirements will impress. For example, dress in a suit or tuxedo for Mistress’s periodc inspection. Take the initiative to advance your relationship by suggesting further acts of submission to Her. Offer to wear tags or a collar to demonstrate your devotion. Finally, be loyal and honest with your Mistress. Do all of these things, and you might just be a good chastity slave who receives the ultimate reward…


Get every new post delivered to your Inbox.

Join 31 other followers