Category Archives: Chastity chronicles

Trials and tribulations of a chastity slave – Installment #22

Monday, 24 February 2020 21:39
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Installment #21 – My favorite reply: “Yes! … What?” in my developing life as Mistress Ayn’s slaveboy

i often encounter challenging situations and quickly, say: “Yes,” but begin to realize i do not truly understand what i said Yes to, thus add: “What?”  Thankfully my “Yes … What?” responses to Mistress Ayn is based on developing trust and has resulted in amazing experiences as i grow as Mistress Ayn’s slaveboy.

In summer 2017, i arranged for two, two-hour BDSM sessions with Mistress Ayn, based on Her website.  W/we seemed like a good fit, thus the “Yes.”  But, i had no idea what i was getting myself into – giving up complete control to a new Mistress that was only a website persona.  When W/we met i accepted bondage, discipline, chastity between the sessions, and much more.  It was wonderful new path for me to travel.

After reading the FemDom Mansion website, i surrendered to a weekend with Mistress Ayn and the Ladies at the Fem Dom Mansion.  i said “Yes” but clearly had no idea what was in store for me.  Rather than a few hours of submission, 48 continuous hours as a slave was incredible and life changing.  Now understanding the “What?”, i committed to serve at the Mansion again and have three more times with more weekends planned.

After the first weekend and as O/our relationship deepened, i asked Mistress Ayn to be my Keyholder, but did not know what i was getting into at the time, thus another “Yes … What?” experience.  She agreed to “try it out for two weeks.”  That was a year ago and She has not mentioned any ending date, nor have i asked.  “Indefinite” chastity appears to be Her preference.  i had no idea where my “Yes” would take me; i am delighted where it has.

Indefinite chastity had led to pantie wearing, nipple piercing, and long distance anal play.  With each new opportunity, i am saying “Yes!” and then learning “what” this truly means.  Never any regrets and it is getting easier to say “Yes” to my Mistress.

She instructed me to begin a Twitter account.  i have never been this “public” with my submissiveness or my experiences with Mistress Ayn, but again said “Yes” and then “What?”.  It was incredible to open up to hundreds of people who are “following” me and Mistress Ayn often re-tweets my posts to Her 10,000 followers.  i have submitted selfies and shared much about my life as Mistress Ayn’s slaveboy.

i suppose others might find my approach to be questionable, risky, or simply poor judgment, but my “Yes! … What?” seems to work for me as Mistress Ayn’s slaveboy.  i cannot wait for the next question posed and am ready with my response.

By slave boy

Trials and tribulations of a chastity slave – Installment #21

Thursday, 30 January 2020 17:00
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Installment # 21 – How Can i Please a Woman?

While i do not claim to know the universal answer to this question, i have learned much as Mistress Ayn’s slaveboy.  Unlike what some men still believe, it is clear to me that i cannot please a Woman with my cock.  Thankfully Mistress Ayn took total control on my – now Her – cock and i am in indefinite chastity.  Thus, i needed to learn what other “tools” were available to me to please a Woman, specifically Mistress Ayn.

Mistress Ayn has educated and trained me to understand many things but two stand out for me.  First, i need to submit – completely and without reservation – to Her.  As Her slave i am better attuned to Her desires and better able to follow Her commands.  i am often surprised by what She asks of me but have learned to not question any command or hesitate in being compliant with any order.

Second, i am learning how to be more attentive to Her needs by listening and not talking.  While She may infrequently desire a conversation with me, most often i need to not talk and to listen carefully to what She is telling me to do or how to act.

By honing in on these two elements of my personal slave training, often at the FemDom Mansion, i found that i am pleasing Mistress Ayn and other Mistresses She requires me to serve. For example, Goddess B’s beaming smile as She administers my morning shower on the patio with the garden hose on the jet setting, paying particular attention to my genitals and asshole.  Or, the roar of laughter as i enter the dining room in ridiculous sissy attire to serve the guest Mistresses and Mistress Ayn dinner for the evening.  Or, during the evening festivities, pleasing many Mistresses as They administered my birthday gang bang, with a dozen other Mistresses looking on approvingly.  Or, when i was ordered to perform a burlesque dance routine so that all of the Mistresses in attendance could be amused by my gyrations, evidence by Their cheers, smiles, and catcalls – all caught on video for viewing later and more pleasure for the Mistresses.

i could go on since there are many ways that Mistress Ayn has instructed me to please Her – including the indefinite wearing of Her chastity cage and frilly panties, and Her latest command – a remote controlled vibrating anal plug.  While men may find different ways to please the Women in their lives, i know with confidence that my ability to please Mistress Ayn and other Mistresses is through my obedience and submissive to the Superior Women in my life.

 

Trials and tribulations of a chastity slave – Installment #20

Sunday, 05 January 2020 18:20
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Installment #20 – About markings – physical and psychological – by slave boy

The dictionary defines “marking” as “the act, process, or an instance of making or giving a mark.”  This rather simplistically defined word takes on a profound, complex, and new meaning in my life, as i am now experiencing “markings” during my submissive and chaste service to Mistress Ayn.

Ironically, many, many months ago and long before i submitted to Mistress Ayn, “no marks” was a hard limit for me when serving any Mistress as Her submissive.  Then, Mistress Ayn asked about this “hard limit” and slowly brought me around to understand that receiving marks was something that pleased Mistress Ayn and can be administered in a safe and sane manner.  Now receiving marks is something i crave as Her personal slave.

A “mark” is a territorial indication that i am Mistress Ayn’s slave.  Sometimes the mark is clearly indicative of that belonging, as when Mistress Ayn leaves Her initial (the mark of an “A”) on my ass during a personal slave training session.  Other times the “mark” is less personal but nonetheless very profound and painful, as when Mistress Ayn flogs or whips my back or thighs, or canes my ass.  These marks do not last more than a few days past the session, as per O/our agreement, but i do find myself checking out the marks later and silently hoping they would last a few days longer.

In addition to the physical markings, the introduction of marks in my submissive life as Mistress Ayn’s slave has another important meaning lasting far beyond their physical presence.  Marking is how Mistress Ayn psychologically exhibits Her control over me and manifests Her possession or ownership of me as Her slave.

i am, as my Twitter name indicates, “Mistress Ayn’s slaveboy.”  That control and ownership is not only shown through physical markings but also psychologically, as She symbolically places Her “mark” on my mind and soul demonstrating Her power over me and in my life.

Markings can be a way of experiencing Mistress Ayn’s infliction of pain, Her physical control over me, and Her psychological ownership of me as Her slaveboy.  What was once inconceivable during a session with a Mistress, and thus a “hard limit,” markings are now a frequently desired occurrence in service to Mistress Ayn.  Receiving Her mark is something i am hoping for every time as i anticipate my next opportunity to serve Mistress Ayn as Her personal slaveboy.

Trials and Tribulations of a chastity slave – Installment #19

Sunday, 15 December 2019 11:59
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Installment #19 – To Be in Chastity or Not To Be in Chastity?  That is the question (to paraphrase William Shakespeare) – by slaveboy jaime

After many, many months of indefinite, mutually agreed upon chastity, i have ample experience to know what it feels like to be in chastity.

There are times where i treasure this state of service and sexual and physical enslavement to Mistress Ayn.  While in chastity there is a calmness to my life, a sense of certainty or routine.  It is a known good and this condition feels normal.

Yet, there is a growing frustration while in chastity, especially after a recent, albeit rare, command to edge and denial, or the even more rare permission to orgasm.  In addition, there is the frequent pinching or constriction and resulting discomfort when sitting in a chair, getting in or out of a car, tossing and turning in bed, or becoming aroused by something or someone – and these experiences occur frequently during the day and throughout the night.  They are a nearly constant reminder that i am Mistress Ayn’s chaste slaveboy.

The frustration or discomfort from being in chastity is replaced when out of chastity with new sensations.  On rare occasions Mistress Ayn permits the removal of the chastity cage so that i might comply with Her order for some sort of edging.  The edging is often for multiple, consecutive days and with a proscribed length of time for edging.  Yet, in most instances, there is denial awaiting the end of the edging time, then icing Her cock so that it fits back into Her chastity cage.  Rarely is there permission to orgasm, although occasionally a ruined orgasm is directed.  Admittedly, given permission to stroke feels very nice and is very intense.  i am quick to gain an erection and shortly thereafter am on the edge of an orgasm.  Then the truly intense frustration sets in as i am reminded of the command for orgasm denial, but with more time left to edge.

These experiences bring forth the question – Is it better to be IN chastity or OUT of chastity?  Thankfully, that is a question that does not deserve or require an answer for it is a rhetorical question.  The correct question is – How might i serve my Mistress, Mistress Ayn, my Beloved Keyholder?  If it is to be IN chastity for an indefinite time, that is my pleasure in service to Mistress Ayn.  If it is to be OUT of chastity for a period of frustrating edging and denial, that too is my pleasure in service to Mistress Ayn.  It is no longer up to me to make these kinds of decisions about my daily, sexual practices.  Mistress Ayn has assumed control of me as Her slave and my life is enriched because of Her guidance in my personal slave training.

Trials and Tribulations of a chastity slave – Installment #18

Monday, 28 October 2019 21:20
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FemDom MansionInstallment #18 – My Personal Slave Training Progress in Review

While most of my chaste slave training with Mistress Ayn is via emails, there were four very special weekends at the FemDom Mansion in the past 18 months.  There i subjected to Mistress Ayn, and other Mistresses and Goddesses of Her choosing, to advance my personal slave training.  At the end of each weekend, i knelt before the Mistresses and Goddesses who took charge of my training weekend and humbly requested that They sign my “personal slave training Certificate of Achievement.”

On the flight home i begin to reflect on my slave training experiences at the hands of these beautiful and talented Mistresses and Goddesses and construct a “Top 13” list of the most memorable or meaningful experiences that have advanced my personal slave training. Recently i reviewed my “Top 13” lists and discovered some patterns reflecting my progress as Mistress Ayn’s personal chaste slave.

  • Humiliation – in the basement dungeon as i was ordered to experience a gangbang, spitroasting, or sucking dildoes; or during the cocktail party where i am typically in full-drag feminization and sitting on the spiked tray, spanked, performing a burlesque dance, or displayed with saline-filled balls; or during the day as i am “waterboarded Goddess-style” (an outdoor showers with garden hose); or feminized (often looking “ridiculous”) for serving dinner;
  • Physical pain – markings from a whip or cane or flogger; electricity attached to inserted sounds; sitting on a spiked tray; multiple piercings with needles; and generally prohibited from using a safe word;
  • Feminization – in full drag for a burlesque dance, Halloween costume as Mistress Ayn’s mini-me, or as a cocktail waitress; or partially feminized as a maidservant for meals;
  • Anal play – birthday gangbang; strap-on sucking and pegging; spitroasted while on display in the dungeon; and,
  • Markings – from a rattan cane or whip or flogger; redness from a spanking; bearing Mistress Ayn’s and Goddess Samantha’s initials.

The level of humiliation, physical pain, feminization, anal play, and markings are all “former hard limits,” with the emphasis on “former” as i have advanced as a slave due to my training.  Not only have i accepted them as part of my new life as Mistress Ayn’s personal chaste slave due to Her expert training, but i am craving these experiences each time i submit to Her and Others for more training.  They seem to please Mistress Ayn and that is my ultimate goal. They have become a part of my life as Her slaveboy and i hope i can endure / embrace even more as my personal slave training progresses – but that is, as always, at Mistress Ayn’s discretion.

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