Tag Archives: chastity

Trials and Tribulations of a chastity slave – #34

Tuesday, 05 January 2021 20:53
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Mistress Ayn “GRANTS” permission yet with a “BUT” attached – by slaveboy jaime

Throughout my years as Mistress Ayn’s slaveboy, i have come to understand that nearly every permission that Mistress Ayn GRANTS me comes with a BUT as well.  For example:

•   Mistress Ayn GRANTED me permission to fulfill my fantasy and become Her chaste slaveboy BUT She decided that i should be in chastity indefinitely AND She ordered me to purchase a bright, sparkly pink chastity cage.

•   Mistress Ayn GRANTED me permission to get in touch with my feminine side BUT She also ordered me to wear panties 24/7 AND preferably pink panties.

•   Mistress Ayn GRANTED me permission to wear Her mark as a constant reminder that i am Her slaveboy BUT the mark was the extremely painful, a surprise nipple piercing, AND the stud are in pink.

•   Mistress Ayn GRANTED me permission to celebrate O/our one-year anniversary of chastity with a “wedding ceremony” BUT i was dressed from head to toe in white or pink as the bride with Mistress Ayn and my four bridesmaids were all in black leather AND in front of 25 of Her good friends She buckle a bright pink slave collar on me with a tag that read: “Property of Mistress Ayn.”

•   Mistress Ayn GRANTED me permission to continue my morning walk routine BUT She added more distance to the walk AND had me insert a vibrating Hush up my ass before taking my walk.

•   Mistress Ayn occasionally GRANTED me permission to remove the chastity cage BUT typically with orders to daily edge myself at greater lengths of time each day AND the multi-day edging culminates with a ruined orgasm, videoed for Mistress Ayn’s amusement, and ordered to eat my cum.

•   Mistress Ayn GRANTED me permission during a video chat to have a “real orgasm” BUT only with 13 pink clothespins attached to Her (my) balls and an Edge device vibrating up my ass and on my taint with Mistress Ayn at the controls.

As you can see, Mistress Ayn does GRANT me permission to achieve a fantasy or experience some pleasure BUT always with a qualifier or condition that reminds me that She is still completely in charge and everything i am granted to do is for Her amusement and pleasure.

As Her chaste, panties-wearing, pierced, collared, sissified slaveboy, i would not want it any other way.

Chronicles of a chastity slave – Then and now

Tuesday, 15 December 2020 19:08
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Image by John Hain from Pixabay

Installment #27: Then: a session with a mistress … Now: session with Mistress Ayn – written by slave boy

For many years i would troll the Internet looking for a mistress to serve when visiting a city.  Once located and receiving permission to visit, i would create a detailed plan of what i was looking for, into, and wanted – an excellent way to maintain control over the session.  There would be a requirement for the mistress to be clad in leather, and agree to subject me to bondage, humiliation, nipple play, moderate CBT, moderate spanking, tease and denial, and perhaps something new.  i would leave the session, as insisted, frustrated without an orgasm, only to return to my hotel room, reflect on the session, and jerk off – maybe twice.

Now my life as a submissive has changed.  Now an upcoming session with Mistress Ayn is completely in Her hands.  She has total control; i have none and do not want any.  At the core of the relationship is trust and my only expectation is to please my Mistress, however She wishes.  Gone are my demanded on how i might control the session.  Gone are my so-called hard limits, for Mistress Ayn knows what I can tolerate, more than i do.  She knows how to hurt me without harming me.  Gone are my pre-session expectations as i attempt to control the session and achieve my satisfaction.  i am completely in the hands of Mistress Ayn.

Now i have experienced things i truly have desired but was too fearful to request, as well as things i never knew to ask for.  i have learned to accept things i previously would not tolerate but accept them now since they please Mistress Ayn.   i leave a session with Mistress Ayn a bit bewildered by what just happened, excited by the new experiences, craving for more slave training, and with a peacefulness knowing that i have served and pleased my Mistress as best i can.

The “now” is definitely better than the “then.”

Trials and tribulations of a chastity slave – Morning routine

Sunday, 08 November 2020 19:19
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Atlanta Key HolderInstallment #26 – My morning routine as Mistress Ayn’s slaveboy

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.

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.

 

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