Category Archives: Chastity chronicles

Trials and tribulations of a chastity slave – Installment #12

Thursday, 13 June 2019 18:07
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Installment #12 – The submissive side overcoming the dominant side

Since i was a teen-ager i have been dominant. i have been in control of every romantic relationship, led nearly every organization i was a member, and professionally am entrusted with leading others. i see myself as a servant leader in my professional life – always seeking to care for and help others but also always the leader, taking charge, being in control. Now focusing on my submissive side, Mistress Ayn is seeking to enable that aspect of my personality to emerge – it is quite a challenge.

When in Her presence for slave training, i find myself resisting letting go of my dominant side. i try to control the situation, often verbally as i do in my vanilla life. It is a hard adjustment to not take the initiative, not to try to plan activities or actions in my submissive life, and generally to refrain from being the center of attention among dominant Women. This struggle comes out in my all-too-frequent comments, often sarcastic and thus sassing my Mistress. It comes out in my wanting to orchestra how things will occur, which is often seen in my constant planning and strategizing my time and behavior for an upcoming slave training session.

As a submissive, a true slave to my Mistress, i need to learn how to let go and trust Mistress Ayn. After decades of grabbing control and holding on, this is indeed a major challenge. i am confident i have surrendered myself and committed myself to the right Mistress.

As my Keyholder, she has grabbed control – literately and figuratively – of Her (now) cock and balls. She decides if i get a release and how it happens. i still find myself wanting to try to manipulate Her into some command, but thankfully She is too strong and wise to fall for those tricks.

As my Alpha Mistress and trainer, i want to suggest what should happen in a session, who might be there, and other controlling suggestions. Again, She is kind but firm in not relinquishing Her control of my training. i am experiencing new things, things i never would have “allowed” or even thought of, and these are some of the best experiences and lessons learned as i find my submissive self as Mistress Ayn’s chaste slave.

Trials and tribulations of a chastity slave – Six months in chastity

Thursday, 30 May 2019 15:36
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Installment #11 – Six months in chastity, omg.  – by slave boy

Not that long ago i counted my time in chastity in days, then weeks, and thought to myself, “Wouldn’t it be something if i was in chastity for months?”  Now, after six months in chastity, i reflect.

The “agreement” with Mistress Ayn to be my Keyholder, and i Her chaste slave, was one of mutual consent.  It was understood that either of U/us could opt out at any time.  Yet, six months later i cannot imagine asking for release from serving as Mistress Ayn’s chaste slave.  It is a “normal” aspect of my life. 

Being Her chaste slave is my first thought in the morning, as the snug chastity cage reminds me.  This normalcy invades my morning routine with daily maintenance of the Holy Trainer cage.  Throughout the day i am reminded of Her control over Her cock and balls as the cage rubs or slightly pinches when i enter a car or take a seat, or countless other normal, daily activities.  And, it is my last thought at night as i feel Her cage against my leg when attempting to sleep. 

It is nearly unimaginable to me that i would have a Keyholder that lives over 700 miles away.   i only see Mistress Ayn during three weekends a year as the house boy at the FemDom Mansion where i serve Her and Her guests as a sissy maid, or as a BDSM submissive, or as a toy for Their amusement, or many other creative situations that Mistress Ayn artfully conjures during my stay.  When at home, i religiously check my email hoping to receive a command from my Keyholder, despite it involving something frustrating, or embarrassing, or subjecting me to Her devious control.

Mistress Ayn seems interested in continuing as my Keyholder.  She randomly sends emails with orders for me to remove Her cage and perform various activities – mostly to tease, edge and deny Her cock, or sometimes to edge to a ruined orgasm, and very infrequently to edge to orgasm.  And, always to immediately return Her cock to Her chastity cage.

W/we seem to be comfortable in this “relationship,” which She often describes as “indefinite,” as in indefinite chastity.  W/we seem to be in a mutually rewarding relationship, Mistress Ayn as my trainer and Keyholder and me as Her submissive, chaste slave.  And, for now, that seems to be the way W/we want it to be.

 

Trials and Tribulations of a chastity slave – Installment #10

Friday, 10 May 2019 17:57
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Installment #10 – Mistress Ayn is a “cat person”

Before anyone, especially Mistress Ayn, is offended by the title of this installment, let me explain.  A wise Mistress explained to me that “a cat often plays with what it has captured before devouring it.”  When realizing that Mistress Ayn has that same practice when training me, i smiled acknowledging that Mistress Ayn is a “cat person,” both in Her behavior as my Mistress and in real life (i know, i was ordered to clean out the cat litter box as Her slave).  There are many examples of how Mistress Ayn “plays with me as Her captive slave.”

Recently, Mistress Ayn ordered me to perform three days of ball torture (rubbing with my hands, rubbing with ice, and hard slapping) while still in chastity after weeks of denial in preparation for an eventual orgasm.

Occasionally Mistress Ayn permits me to be released from Her cage for successive days.  She then orders me to tease and deny Her cock each day for longer periods of time but never permitted to orgasm as the tension builds.

When preparing for another weekend of slave training at the FemDom Mansion, Mistress Ayn would only provide vague references about what was in store for my weekend of slave training.  Enough to get me thinking and worried, but never enough to let me know what actually might happen.

Mistress Ayn has suggested in an email that i may be allowed to orgasm on an undetermined day in the near future with tasks to perform until then, but i never really know if an orgasm will actually occur or She will take it away from me.

There is a pattern of toying with me as Her slave, like a cat that toys with its captured prey before devouring it.  Mistress Ayn is definitely a “cat person.”

Trials and Tribulations of a chastity slave – Installment #9

Thursday, 02 May 2019 20:05
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Installment #9 – Breaking down “hard limits”

As Mistress Ayn’s chastity slave i am finding that many of my so-called “hard limits” are dropping off that list.  Before becoming Mistress Ayn’s slaveboy, i passionately resisted many things:

  1. Gag – with a quick reflex against objects in my mouth,
  2. Blindfold – wanting to see what was going on in a session,
  3. Piercing – afraid of blood being drawn during a session and the pain associated with piercings,
  4. Marks from whipping – again afraid of drawn blood, a worry over marks being seen by others in my vanilla life, and the potential for intense pain,
  5. Anal play – uncomfortable with any activity in my ass and fearful of the pain involved,
  6. Foot worship – disinterested in touching anyone’s feet or having my own touched,
  7. Feminization – never considered myself to pass as a woman – which is how i viewed this play,
  8. No safe words – always needing a way out of the play, and

Collectively all of these hard limits have disappeared and their presence are a mainstay in my current slave training.

Why? There appears to be two primary reasons.

Most importantly, i am now being trained by a Mistress whom i completely trust.  Mistress Ayn, and other Mistresses i serve, know how to introduce these activities into a session without causing me harm or raising unnecessary fears.  They are presented sanely and safely but still with intensity.  Mistress Ayn also has made it clear that these activities bring pleasure to Her and Her friends and that is my ultimate goal as a submissive.  Oddly, i now crave many of these activities in a session since they are amazing experiences in my journey as Mistress Ayn’s chaste slaveboy.

Secondly, i am learning how to give up control.  Rather than orchestrating a session by imposing these hard limits, i am simply asking for three things: to be controlled, humiliated and experience pain.  This tri-fold desire runs counter to many of my former hard limits.  By giving up the control in a session and more and more in my life, i am accepting, even embracing, new experiences, such as each of these so-called hard limits on the list.

A lesson learned, at the hands of a skilled Mistress whom i trust completely, is a wonderful lesson learned.

Trials and tribulations of a chastity slave – Installment #8

Saturday, 06 April 2019 10:31
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Installment #8 – When “playing” with chastity became a “lifestyle” of chastity. – by slaveboy

Many men and some couples “play” with chastity.  As a male, it was a fun way to fantasize that a Dominant Woman was in control of my cock and restricting me from getting an erection or orgasming.  i would put on the cage for a few minutes, an hour, or even a day, but then remove it when i wanted and revert to my familiar masturbation practices.

Couples often use chastity as a way to spice up their sex life, with the female taking control and the male submissive.  It is a fun way to spend a day together, or a weekend, or for the dominant partner to threaten longer chastity sentences.

Yet, at some point my “playing” with chastity became living a chastity “lifestyle.”  Once Mistress Ayn became my Keyholder and took over control of Her cock with Her chastity cage, my world was turned upside down, but in a good way.

Now i am permitted release from Her chastity cage for a few minutes, or an hour, or rarely a full day.  i never know when this permission will be granted.  Then, it is back to normal for me – back in Her cage, often without an orgasm and very rarely after a real orgasm.

i am unsure when this transformation actually occurred.  When did i realize that W/we were not “playing” with chastity but it was now a lifestyle?  Each month i pay my keyholder fee, as a tribute for the attention that Mistress Ayn gives me as Her chaste slave.  Each month there is no discussion of ending this relationship, nor do i intend to bring up.  W/we do not have a set ending – not after a month, or six months, or a year.  She does not refer to my chastity as permanent chastity but prefers indefinite chastity.

Indefinite, as in a lifestyle, suits me just fine.  It brings me closer to my desire for a female-led relationship, a life where i do not control my cock, and a re-orientation of my attitude toward pleasing a Woman, my Mistress, rather than satisfying my selfish carnal desires.  This seems to work for me right now in my life, even though i am not fully aware of when this transformation actually occurred.

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