Category Archives: Chastity chronicles

Trials and tribulations of a chastity slave – COVID special edition

Friday, 25 September 2020 13:23
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Photo courtesy of Image by Łukasz Dyłka from Pixabay

 

Special COVID edition by slaveboy.

W/we are firmly in the grips of a COVID-era and my slave training now occurs long distance, yet Mistress Ayn is still very powerfully in control.  It would be easy to become negative and lament not having a forthcoming scheduled weekend at the FemDom Mansion – as would “regularly” occur – but W/we are not living in “regular times” these days.  Alternatively, there are daily activities that remind me of my status as Mistress Ayn’s slaveboy, in chastity and collared, such as my morning walks.  During the walk i focus on how many things Mistress Ayn has introduced to establish Her daily presence in my life.

While wanting to “try out” a chastity cage was my idea, i did ask Mistress Ayn to be my Keyholder.  But, She introduced the terrifying word – “indefinite” – into chastity wearing and now i am in chastity indefinitely.  She also ordered me to purchase a pink cage, then a pink with gold sparkles cage, and now a smaller black cage for those special “formal” occasions.

While dressing as a sissy was fun and humiliating at the FDM, Mistress Ayn ordered me to wear panties every day, and i am, and it is amazing.

Obviously it was Mistress’s idea to pierce my nipples.  It is incredible and does remind me, in yet another way, that i am Her slaveboy … indefinitely .. and, of course, the posts are pink.

i began daily morning walk, mostly for physical health reasons, yet Mistress Ayn challenged me to extend the route, which i have.  She also ordered me to insert the Hush during these walks, which i have.

In addition to all those ways Mistress Ayn is with me every single day as my Mistress, i never know when i might get an email from Her with orders.  i check my “slaveboy” email account twice a day – at least – hoping (and dreading) for an email from my Mistress, never knowing what She will command me to do.

Will i be allowed to unlock Her chastity cage?  Will i receive sexual relief to the daily frustration of indefinite chastity?   Will it be a ruined orgasm, or full orgasm, but always, if there is discharge, to consume every drop.

In this COVID-era being Mistress Ayn’s owned, chaste slave is not something that occurs – with, admittedly, a big bang – every few months at the FDM.  Rather it is a combination of multiple daily experiences to keep me focused in my role as Her slaveboy, to remind me of my devotion and commitment to Mistress Ayn in doing whatever She asks of me (that really could be very scary).

It is indeed amazing to recall how truly talented Mistress Ayn is as a Mistress, Keyholder and Owner and how terribly fortunate (not lucky! as She has taught me) i am to be Her slaveboy.

 

Trials and tribulations of a chastity slave – The Routine

Thursday, 06 August 2020 15:46
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Installment #25 – My morning routine as Mistress Ayn’s slaveboy – by slave boy jaime

After more than a year in indefinite chastity as Mistress Ayn’s slaveboy, my morning routine was become quite comfortable for me, well, as comfortable as it can be.

i awake and reach down to feel Mistress Ayn’s chastity cage. She controls me especially through my cock and balls and it is a good reminder to me of what is truly important in my life.  Since it usually has been weeks since my last orgasm, i am frustrated and start to tease my nipples.  As i get more awake and aroused i can feel my cock starting to get longer and harder.  Quickly the pleasurable sensation is replaced with the frustration of realizing that my cock cannot get erect, barely half erect, while in the chastity cage.  This reminds me how i treasure feeling controlled and restricted by Mistress Ayn.  It is Her cock and She decides if it gets out of the cage – which is rare since She relishes my indefinite chastity.  When i cannot take any more frustration, i get out of bed and face the day knowing physically, as well as mentally, that i am Mistress Ayn’s chastity-caged slaveboy.

Each morning Mistress Ayn orders me to perform maintenance on Her chastity cage.  i remove the cage with the key She permits me to have to thoroughly wash the cage.  i shower and pay special attention to clean Mistress Ayn’s controlled genitals.  Then, without any thought of disobeying my Mistress, i never touch Her cock or balls when out of the chastity cage and immediately replace the chastity cage on Her cock and balls and lock it up.

Before i dress, i am required to check the nipple piercings Mistress Ayn compelled me to receive to make sure that the caps are securely on the ends of the pink posts.  i also make sure the piercings are sanitized.

When getting dressed i select the sexiest panties from my wardrobe to make sure that Mistress Ayn’s sissy slaveboy is properly adorned.  i love my assortment of pink panties, G-string pouched panties and other frilly underwear.

i am off to work or some other task wearing my panties, feeling my nipple piercings through my shirt, and the secure and tight chastity cage around Her cock and balls.

This is my new life and i am loving it.  Every day i am reminded that i am Mistress Ayn’s chastity-caged, sissy slaveboy.

Mistress Ayn has customized chastity programs for the short term fetishist to the serious chastity submissive.

 

Trials and Tribulations of a chastity slave – Installment #24

Wednesday, 01 July 2020 22:38
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Installment #24 – Indefinite Chasity – May Be the Harshest Chastity Sentence of All – by slaveboy

From my investigations, chastity sentences take on many different forms and release from chastity is widely variant.  Some subs earn release if they beg their Mistress sufficiently; others gain release if the sub performs specific tasks to an established level of performance.  Others chastity subs are on a pre-determined scheduled for releases.  Finally, some subs are in chastity forever.

The chastity forever may seem to be the harshest chastity sentence but i suggest that indefinite chastity may be even more difficult to endure for the sub.  Mistress Ayn desires indefinite chastity and i have pledged my commitment to being in chastity indefinitely.

Each morning i awake to the feel of my pink, hard plastic, Holy Trainer chastity cage around Mistress Ayn’s cock and balls, for She owes them.  i wonder immediately – is today the day Mistress Ayn will order me to remove the cage for edging, or a ruined orgasm, or an orgasm?  The latter occurs only very rarely.  But, most importantly, it is the not knowing that has the most impact on me and reminds me of Her total control over me as Her slaveboy – physically, psychologically, and sexually.

Subs in chastity forever know that they will never be released or orgasm outside their cage.  i simply do not know for certain.  Today may be the day that Mistress Ayn rewards me with release and orgasm or today may be another day where She rewards me with continuing to be Her chastity slave.  The uncertainty means Mistress Ayn is completely in control of Her cock and balls, Her chastity cage, and Her slave’s releases.

Indefinite chastity is the harshest of the chastity sentences and, honestly, i am delighted that this is what my Mistress, my Keyholder, desires to please Her the most.  i remain in chastity, indefinitely, in service to Mistress Ayn.

Mistress Ayn has customized chastity programs for the short term fetishist to the serious chastity submissive.

Trials and tribulations of a chastity slave – Installment #24

Friday, 29 May 2020 14:25
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Installment #24 – My first overnight Hush training session  – by slaveboy jaime

The Hush is a vibrating anal plug that offers control at both close range and long distance.  This means that Mistress Ayn can order me to insert the Hush and play in the privacy of Her FemDom Mansion but also to take control when She is 700 miles away.  She can create patterns or order me to access established patterns of vibration at varying speed.  A few initial sessions showed me that the Hush was a safe, exhilarating, and addictive anal play toy.

The use of the Hush took a dramatic step forward when Mistress Ayn ordered me to insert the Hush late one night and then go to bed with my phone nearby.  She was able – at Her complete discretion – to access control of the Hush.  She decided when She would engage the Hush, what patterns would play, how long the patterns would play, and could exchange text messages with me during the play.

After i had drifted off to sleep for about an hour, i felt the pulsating Hush in my ass, now controlled by Mistress Ayn, awaking me to a completely new sensation.  Off and on for over an hour, Mistress Ayn would initiate and then stop different vibration patterns.  i never knew when She would start up a new pattern or how long She would allow a pattern to run.  i did not know when this early morning (starting around 1:30 am) would end or if it would ever end – the Hush has a long-lasting battery.

Besides the powerful physical sensations, having Mistress Ayn take control of my life through anal play was an awakening emotionally.  She controlled what i felt, the length of the stimulation and the type of stimulation.  i was reduced to simply reacting to Her sadistic whims, which i treasure and adore as Her slaveboy.

Step by step, in my life as Her slaveboy, Mistress Ayn has taken more intense control of me: initially by placing me in indefinite chastity, then ordering me to wear panties 24/7, then having my nipples pierced while visiting Her one day in Atlanta, and now by invading me through my ass and dictating the level of pleasure and discomfort in the middle of the night.

The rush of Her forceful control and my unlimited submissiveness was intense that first night of Hush play and had me eagerly awaiting if Mistress Ayn would continue this play the next night – She did not – or the following week.  Thus, i was forced to wait, only available to respond, never dictate or control.  i am addicted to being Her slaveboy and now that means being available to Her at any time overnight and submit to Her playful torture using the Hush.

Trials and Tribulations of a chastity slave – Installment #23

Wednesday, 29 April 2020 12:31
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Installment #23 – The Role of Fear in Our (Mistress Ayn-slaveboy) Relationship

In most relationships (as in life) fear is something that is desperately avoided.  Generally, fear is understood as a weak emotion that should be controlled.  Yet, i am learning in my relationship as Mistress Ayn’s slaveboy that fear is something that must be embraced.

In O/our relationship, my fear spawns from the reality that Mistress Ayn is completely in control of all things, especially what happens to me.  Even long distance, She dictates chastity release, panties wearing, nipple piercings, anal play, and so much more.  When in Her presence, She determines what i eat and drink, wear, behave, whom i serve, and so much more.  She decides everything and i simply surrender to Her control, although fear remains part of what i am feeling given the unknown and degree She pushes me to be a better slave.

In O/our relationship, my fear indicates that Mistress Ayn is about to expose me to something i had not experienced before or perhaps not even considered or wanted.  As a frequent masturbator, i never imagined wearing a chastity cage indefinitely.  As a traditional male, i did not consider becoming a pantie wearing submissive.  In my vanilla life, getting a piercing was not on my list of desires.  Yet, She knows what i need and will impose it upon Her slave despite my fear.

In O/our relationship, my fear signifies that i must turn to trust, as in trusting in my Mistress.  Trusting that: She will hurt me, but never harm me; She will push my limits, but never beyond what i can take; She will give another Mistress control over me, but has established ground rules with the Mistress that She knows well; and She will always be there for me as i face my fears.

This is my thinking that helps me learn to embrace my fear in O/our relationship and by doing so i have come to understand that a healthy amount of fear makes sense in O/our relationship and allows O/our relationship to grow and for me to trust Mistress Ayn even more with each new experience.  Embracing my fear as an essential element in O/our relationship has enabled me to build a strong commitment in trusting my Mistress and that is all that truly matters for me, Her slaveboy, in O/our relationship.

 

Your obedient and submissive slaveboy

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