Tag Archives: chastity

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.

Trials and Tribulations of a chastity slave – #33

Sunday, 05 December 2021 20:53
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The Emergence of a Sissy Slut – by slaveboy jaime

i have long believed in the Supremacy of Women, so becoming a submissive to Mistress Ayn was not a surprise to me, however the depth of that commitment does pleasantly shock me.  i do not know how deep inside of me was the desire to also become a sissy slut, but Mistress Ayn located that and is exploiting it to my amazement and Her (and my) enjoyment.

It is one thing to have Mistress Ayn spend what seems like hours up close and personal with me.  i treasure those times when She carefully and precisely applies makeup and transforms me into the sissy She desires.  Then a variety of Mistresses and Goddesses enjoy the task of selecting what i am to wear – sometimes silly and other times quite elegant (as my “bride’s outfit” for the collaring ceremony at the FemDom Mansion) – in order to serve Them at dinner or be the perfect hostess at a cocktail party or perform as a Burlesque dancer.

Yet, recently, there has been a major transformation in my “sissyhood.”  i am now purchasing a new sissy wardrobe for myself to wear privately around my house or upon command for Zoom sessions with Mistress Ayn – not only on display at the FemDom Mansion.  With guidance from Mistress Ayn, i search websites for that perfectly sissified pair of stockings, or garter belt, or corset, or bedtime wear, or French maid’s outfit.

When i wear these clothes i feel my “sissy-self” emerging.  i feel more in touch with “my feminine side,” a cliché but true.  i feel complete in having this part of my personality emerge.  i feel sexy, yet submissive.  And, the corsets, it is like someone is hugging me with the soft texture of the material but the firmly embracing me through the tightly laced ribbons securely tied.

This is all still quite new for me but i am treasuring what i am now experiencing.  It is good to find a new and comfortable side of my personality and even more exhilarating that it seems to please my Mistress.

i often wondered if She dressed me up – once as Mistress Ayn’s Mini-Me for a Halloween party at the FemDom Mansion – because She liked it, which is sufficient for me.  But, now i am thinking that Mistress Ayn saw this part of me way-down, deep inside my psyche and has helped bring it out so i can enjoy it because She cares for me so very much as Her chaste and owned slaveboy.

Trials and tribulations of a chastity slave – #32

Monday, 08 November 2021 22:09
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When Mistress Ayn declares indefinite chastity – by slave boy

After achieving my “two years in chastity” anniversary, i thought it prudent to reflect upon my experience as Mistress Ayn took charge of my orgasms.  She decided if i could orgasm, when i should orgasm, and how i should orgasm.  She also made it clear that i should be in chastity indefinite, so the pattern described next seems to be my life now, as Mistress Ayn’s chaste slaveboy.

During my days of pre-chastity, i would masturbate to a powerful orgasm 3 times a week, that is 156 times in a year. But now ….

In 2019, i was allowed: 8 “real” orgasms, 8 “ruined” orgasms, and one “forced” orgasm, a total of 17 “releases.”

In 2020, i was allowed: 6 “real orgasms, 6 “ruined orgasms, and 4 “forced” orgasms, a total of 16 “releases.”

In 2020, my “releases” were:

Jan 20 = 3 “forced” (rapid) orgasms

Jan 31 = “ruined” orgasm

Mar 15 = “real” orgasm

Apr 8 = “real” orgasm

Apr 30 = “real” orgasm

May 18 = “real” orgasm

Jun 22 = “ruined” orgasm

Jul 22 = “ruined” orgasm

Sep 3 = “ruined” orgasm

Sep 21 = “forced” orgasm with vibrator

Oct 22 = “ruined” orgasm

Oct 29 – “real orgasm” with clothespins attached to Her balls and the Edge in my ass

Nov 12 = “forced” orgasm with vibrator

Dec 26 – “real orgasm”

Dec 29 – “ruined” orgasm

Dec 31 – “real orgasm”

i definitely see a pattern here – about the same number of orgasms each year while in indefinite chastity (an average of 1.3 per month or 0.3 per week) and less than half of the permitted or ordered orgasms are “real” or pleasurable orgasms.

No complaint, no opinion, simply reporting and committing to my complete devotion and obedience to You, Mistress Ayn, as Your chaste slaveboy.

Trials and tribulations of a chastity slave – #31

Tuesday, 22 June 2021 13:27
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Installment 31 – When a submissive is asked by his Mistress: “What do you think?” – by slaveboy.

In the heat of an intense tease and denial session, Mistress Ayn asked me: “Do you want to cum, slaveboy?”  The obvious, immediate, physically induced, sexually frustrated answer is: “Yes, please, Mistress, please let me cum.”  Yet, deep down inside, at the core of my submissive nature, there is a desire for denial, to be kept from an orgasm by my dominant Mistress.  i crave to be stopped just short of an orgasm and ordered to be locked back into Her chastity cage.

This moment caused me to reflect later – “should a submissive be asked what s/he thinks or wants?”  i am less comfortable with that task for two reasons.

First, as a submissive i often decide incorrectly or too tentatively.  i did not want to be placed in indefinite chastity (i wanted to try chastity but not necessarily indefinitely), or to have my nipples pierced, or be dressed in drag by Mistress Ayn and Her friends, or be chained in the dungeon overnight, or to eat from a dog bowl, or be subjected to painful discipline from a whip or cane, and so many, many more things.  Mistress Ayn jokes about my “hard limit” list, which has disappeared as i have given up control to Mistress Ayn.  These experiences are some of the very best things i have endured, as Mistress Ayn’s owned slaveboy and i treasure them.  When i let go, gave up control, stopped thinking for myself and trusted Mistress Ayn, things became so much better in my life.

Second, as a submissive it is unnatural for me to think – that is a form of control.  i am a slave, Mistress Ayn is my owner.  Her role is to control me, my role is to obey Her.  She uses me for Her pleasure, my primary responsibility is to please Her.  Thinking or exerting any sort of control into O/our relationship often ends up with me in trouble.  Thinking is not what She needs from me nor what i am particularly good at as Her slave.  Listening to my Mistress and fulfilling Her commands is my role as Her owned slaveboy.  Over time, as i become more obedient and sensitive to Her wishes, i become a better owned and chaste slaveboy and Mistress Ayn is pleased with me.

However, a Mistress should ask Her slave anything She wants.  She does not and likely will not do what the slave asks for, but She may be interested in knowing what the slave is thinking.  And, i have learned that the best response is – Whatever pleases you, Mistress Ayn.  That truly has become what i am thinking and what i want the most.

Trials and tribulations of a chastity slave #30

Wednesday, 05 May 2021 14:05
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Installment # 30 – Mistress Ayn: The “Steven Spielberg of FemDom”

As many know, Steven Spielberg is one of the world’s premier movie directors.  My observations of, and experiences with, Mistress Ayn convince me that Mistress Ayn is the “Steven Spielberg of FemDom.”

Session after session, weekend after weekend, Mistress Ayn orchestrates as a skilled director established Mistresses and Goddesses, as well as newcomer Mistresses, switches and slaves.  Actors accept Her direction, follow Her lead, and gracefully fit into their roles as participants in Mistress Ayn’s production.  She seems to know how to get the most out of each actor, when to move aside and allow a seasoned Mistress to take charge, or when to step in with guidance or inspiration for other actors during the session or weekend.

The plot is crucial in telling the story and making a powerful production.  Over many weekends of my slave training at the FemDom Mansion and a few extended sessions at the Atlanta Dungeon, Mistress Ayn introduced various, and often unexpected, twists and turns to the plot but always with a clear objective – create a better slave to please all Mistresses.

Mistress Ayn knows when and how to use a location for Her production.  She uses a local nail or Brazilian wax salon to humiliate me as a slave-in-training, or has Mistresses take me to a mall to buy bling and clothing for a drag scene later at the Mansion.  She is very creative in getting the most out of locations at the FemDom Mansion.  The outdoor patio is the perfect space for my humiliating showers.  The dining room is a wonderful place for further embarrassment as Mistress’s sissy maid servant.  And, the downstairs dungeon is a natural location for Mistresses to indulge in Their personal fantasies with a willing slaveboy to serve Them.

Audiences often overlook the artistic aspects that make a good movie.  Mistress Ayn is aware of how to utilize hair, makeup, and costuming.  On more than one occasion Mistress Ayn, or Her co-producers (other Mistresses), dressed me up for a burlesque performance or for humiliation as a sissy maid servant.  i was stunning as Mistress Ayn’s bride in O/our collaring ceremony, adorned in lace and leather.

As an excellent director, Mistress Ayn knows how to improve my dialogue in a session – “Yes, Mistress,” “Thank You, Mistress,” and “Whatever pleases You, Mistress.”  She also knows when words are not needed and has effectively stopped (almost) my sassing during my stay the FemDom Mansion.

Like Spielberg, an outstanding director of a good film (or session) requires planning, control, motivation, and securing trust from Her actors.  Mistress Ayn artfully constructs a scenario that accentuates Her pleasure and the sub’s training.  She knows who to include in a session, how to build the session, what tools or implements to have available, and when to reinforce training with pain or when to insert pleasure.

Mistress Ayn is the quintessential Hollywood movie director.

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