Category Archives: Chastity chronicles

An open letter about chastity

Tuesday, 07 November 2023 10:44
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by Mistress Ayn’s slaveboy

Five years ago, in 2018, i reached out to Mistress Ayn, whom i had served only a few times in session as a submissive, after many decades of submitting to other professional Mistresses, and asked if She would consider being my Keyholder and placing me in chastity.  In retrospect, i honestly really did not fully understand what i was asking of Her or the multiple dimensions or aspects of chastity, but thankfully She was knowledgeable, experienced, and willing.

For Her services, which have far exceeded my expectations and fantasies, She explained that there would be a monthly fee (a financial aspect of chastity), not exorbitant but fair given Her time commitment.  This was the first reality check of being a chaste slaveboy to Mistress Ayn – i needed to commit to Her demand of a reasonable financial commitment.

Then, She explained that there was no set “end time” or regular schedule for chastity with Her and Her subs (beginning the psychological aspect of chastity).  For Mistress Ayn, chastity was “indefinite.”  No, i had no real idea of what this meant. But quickly learned that there was no “you are in chastity for so many days or weeks, and then get a release to orgasm.” But i agreed to that psychologically controlling condition as well.

Yes, there is a physical/sexual element of chastity, too.  i no longer can seek private times and freely stroke my cock and experience the exceptionally powerful and satisfying orgasms – as i vaguely recall them to be.  No, Mistress Ayn is now in control of my cock. Now, it is Her cock, and She decides when, where, and, importantly, how i might experience any sort of pleasure associated with Her cock. These opportunities have become fewer and less satisfying as determined by Mistress Ayn, yet my enjoyment of serving Mistress Ayn in this way has increased significantly.

i began to understand that Mistress Ayn was indeed, as She said, the Queen of Long-term Relationships. Thankfully, this is a wonderful thing, since She is completely unpredictable, amazingly creative, and very caring, and i never want O/our relationship and all its different aspects to end.  So, five years later, there seems to be no end in sight as determined by the calendar and i am delighted.

In addition, chastity has affected other relationships in my life (the social aspect of chastity).  i am less focused on myself and more on others – mostly on other Women whom i meet, but not having a sexual or intimate relationship with Them.  Chastity enables me to focus on other ways to please Women than sexually – by listening better to Them, by being more sensitive to Their needs and wants, by being present to Them as They share Their lives with me, and so on.

Chastity has made me a better submissive but also a better male and person.  It has taken away the distraction of selfish pleasure and i have become a person who is better at relationships, at just being a better human to other humans.

Five years is not a mark on a calendar indicating an end to an era or task, but simply a footnote of how long i have been loyal to Mistress Ayn, as my Keyholder, and am learning how to be a better person.  Thus, there is no obsession with “achieving an end date” but rather an intense desire to continue to become even better as a person to Mistress Ayn, to other Mistresses She allows me to serve, and to others outside my submissive life as well.

Mistress Ayn’s chastity heyholding programs

Trials and Tribulations of a chastity slave – The 12 Degrees of Male Sexual Pleasure

Tuesday, 12 July 2022 22:48
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Installment #37 – The 12 Degrees of Male Sexual Pleasure

Moving from what provides the most pleasure to the least:

  1. Sexual intercourse, penetration, building to mutual orgasm
  2. Blowjob, with multiple edges, leading to a powerful orgasm
  3. Hand job, with multiple edges, leading to a powerful orgasm, where the cum is fed to the slave and eaten
  4. Self-masturbation, with multiple edges, leading to a powerful orgasm, where the cum is collected and eaten by the slave
  5. Masturbation with a vibrator, with multiple edges, leading to a powerful orgasm, where the cum is collected and eaten by the slave
  6. Self-masturbation, with multiple edges, at point of climax the hand is released causing a ruined orgasm, where the cum is collected and eaten by the slave
  7. Masturbation with a vibrator, with multiple edges, at point of climax the vibrator is removed causing a ruined orgasm, where the cum is collected and eaten by the slave
  8. Stimulation with a vibrator while the cock is still in a chastity cage, with multiple edges, leading to a powerful orgasm, where the cum is collected and eaten by the slave
  9. Stimulation with a vibrator while the cock is still in a chastity cage, with multiple edges, at point of climax the vibrator is removed causing a ruined orgasm, where the cum is collected and eaten by the slave
  10. Stimulation with a vibrator while still in a chastity cage, with multiple edges, before the point of climax the vibrator is removed and no orgasm, denial
  11. Anal insertion of plug with vibration, while still in a chastity cage, with multiple edges until leaking occurs, where the cum is collected and eaten by the slave
  12. Anal insertion of plug with vibration, while still in a chastity cage, with multiple edges, but stimulation ends before leaking, denial

 

FYI, I cannot recall #1, #2, #3 or #4. #4 may have occurred in 2020.  In 2021, so far, I have experienced #6, #5, #6 and #7, but recently Mistress Ayn seems more interested in #8, #9,. Or #10.  There is clearly a trend, enough said.

Trials and tribulations of a chastity slave – Finding to correct way to say “I love You, Mistress”

Wednesday, 30 March 2022 20:16
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Installment #36 – Finding to correct way to say “I love You, Mistress” by slaveboy jaime

Recently, i have felt a greater commitment and devotion to my Mistress, Mistress Ayn, yet words have failed me in my effort to clearly express what it is that i truly feel.  In my quest for understanding i turned to the Ancient Greeks – odd? perhaps! – to find clarity.

The Greeks have seven different words for love, each expressing a different sentiment.  Most commonly, people say “I love you” and mean “eros.”  Eros speaks of a romantic love, a feeling of passion.  This may be common among partners in a loving relationship, such as a wife and husband, or girlfriend and boyfriend.  But that misses the mark for my feelings as a submissive and my Mistress Ayn.

There is “phila” or a love between friends.  i feel that toward other Mistresses and Goddesses i have met and served at the FemDom Mansion or Atlanta Dungeon.  i treasure these relationships and love serving Them.  Yet, again not the special type of love i have for my Mistress Ayn.

“Storge” comes closer since it expresses a love that in unconditional and relational.  i am unconditionally committed to my Owner, Mistress Ayn, and will do whatever She orders me.  But, still not quite on point for my feeling of “love” toward Mistress Ayn.

Then i found it – “agape.”  Agape is a love that is typically reserved for a universal love, the love one has for a God (or in this case, a Goddess).  It is a love between unequals.  Yes, that is it – “Agape” – the proper expression of my love for my Mistress.  Agape is the deep felt expression of my devotion, a willingness to completely surrender to Her, to be or do whatever She wants or needs from me – slave, sissy, bitch, servant, and so many more roles.  Agape is how i understand Her role in my life, as my Mistress, Owner, Keyholder, Teacher and so many more.

Agape – i love You, Mistress Ayn. – slaveboy

Three Years in Chastity: “Mission Accomplished”

Sunday, 13 February 2022 19:07
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In the continuation of the Trials and Tribulations of a chastity slave chronicles, slaveboy reminisces about orgasms . . .

The three-year anniversary of my “indefinite” chastity caused me to reflect on a fading memory — orgasms.  Before chastity, i orgasmed when i felt the urge – about twice or thrice a week. i really do not remember those days, (as You like to say Mistress Ayn: “Mission Accomplished!”).  Then, as Your chaste slaveboy, i would look forward to the days whenever You would permit an orgasm.

Recently things have changed – orgasms are permitted whenever You wish to have them happen and under Your control (“Mission Accomplished!”).  And, a new twist – they rarely involve my stroking to a satisfying orgasm.  Your plan seems to have me orgasm JUST often enough for me to remember what You have taken away from me (“Mission Accomplished!”).  Orgasms are now just another one of Your many ways to control me, sometimes reward me, and even sometimes they are used to punish (“Mission Accomplished!”).

There is no pattern, for that would allow me to anticipate.  At the end of 2020, You had me orgasm at the stroke of the new year. The next year You casually signed off in Your last email, informing me that “I am off until Monday.”  No orgasm to end the year, keeping me unbalanced and submissive (“Mission Accomplished!”).

In 2019 and 2020, i was permitted “release” 19 times and 18 times, respectively.  For 2021, that number plummeted to 12 – a 35% drop.  i see where this is going: fewer releases, farther and farther apart, making it harder to remember orgasms, and You exerting more control (“Mission Accomplished!”).

And a new element, merely 12 releases, yet only FIVE “real orgasms,” when i was allowed to touch Your cock and bring myself to a satisfying orgasm.  THREE times a ruined orgasm, stroking but stopping just short of a satisfying release. THREE times a forced orgasm – release but no physical touch Your cock, but using a vibrator.  And, ONCE a forced, ruined orgasm – no physical touching and stopping before ejaculation.  You are a creative Mistress and apparently One with a plan – fewer releases and even fewer the old-fashion way = jerking off to ejaculation (“Mission Accomplished!”).

Is there a lesson here?  Yes.  You are in control, it is not about me, my needs, or my pleasure (“Mission Accomplished”). It is about Your pleasure.  My less frequent releases seem to please You, with new twists and turns, and less satisfaction.  i gladly embraced this new training.  You have trained me well, oh wise Mistress.  – slaveboy jaime

 

Trials and Tribulations of a chastity slave – Installment #34 – Cuckolding a collared, chaste, sissy slaveboy

Tuesday, 18 January 2022 21:20
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Installment #34 – Cuckolding a collared, chaste, sissy slaveboy – by slaveboy jaime

As many people know, cuckolding is often when the dominant female has sexual relations with a male that is not Her husband or partner.  She may also subject Her husband or partner, often serving Her as Her slave or sub, to watch or hear about these activities to further humiliate or dominate the sub.

As Mistress Ayn’s collared, chaste, sissy slaveboy, sexual activity is not part of O/our Mistress-slaver relationship.  i could never satisfy Her in that way – as She reminds me, my (now Her owned and caged) penis is too small to satisfy Her.  And, i will never be Mistress Ayn’s husband or partner.  Yet, cuckolding is present in O/our relationship in a unique way.

Each time She dominates another one of Her collared slaves or any submissive, i feel a sense of jealousy.  When She describes what She did to a slave, i am envious of what the other slave experienced.  i want to be there for Her, suffering at Her hands, being humiliated by Her words or actions, just serving Her and pleasing Her as She wishes – not hearing about another slave having that privilege.

i know Mistress Ayn does everything for a purpose and while She is not disciplining, humiliating or sissifying another one of Her slaves because of me specifically, it may also be a way She choose to cuckold me – to show me Her dominance and control over me by dominating and controlling another slave.

i have learned that my place as Her collared, chaste, sissy slave is to be there when She wants me and to accept that She has other collared, chaste or submissive slaves available to Her that i must accept as Her slaveboy.

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