Category Archives: Chastity chronicles

Chronicles of a chastity slave – pain and the sissy

Wednesday, 20 January 2021 12:12
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Installment #28 – On Becoming a Pain, Anal and Sissy Slut – by slaveboy

The transformation from being a bondage slut to becoming a pain, anal and sissy slut has been gradual but steady under the skilled hands of Mistress Ayn.  A slut = a person with a seemingly insatiable but often undiscerning desire to do or have something specified (Dictionary.com).  It is what i am becoming and i love it.  Each area was once a limit yet is now welcomed and desired.

Pain Slut – Initially i would avoid any serious pain, accepting only light spankings.  Then was introduced to serious flogging and loved it; then came whipping and caning and i cannot get enough now.  i have learned to “welcome and embrace” the pain, rather than fight it, which means i can take more.  i have had back-to-back days of whipping and had body orgasms from the pain.  Afterwards i want to see the marks and am sad when they dissipate.  Still a long way to go but definitely on the journey to becoming a pain slut.

Anal Slut – My hard limit was “no anal,” then i tried it and realized that i craved it, badly.  Dildo penetration is amazing as Mistress Ayn controls me, whether from behind on a bondage bench or facing me when in a sling.  Multiple Mistresses gang banging me is intense.  Being spitroasted is both humiliating and exciting.  When Mistress Ultra Violet was concerned that Her dildo was too thick, i was silently wishing, “please try it.”  She did, it was not, and it was incredible.

Sissy Slut – Feminization was “not my thing” and is now what i am looking forward to during each slave training session.  Mistress Ayn’s smile after applying my makeup, other Mistresses laughing as They dress me, the feel of a nightie when in bed at hotel between slave training sessions, pictures of me as the blushing bride at my collaring ceremony dressed in white, or looking so humiliated as slave “nana” to serve Mistresses dinner.  i am so comfortable, it feels so natural while sissified.

Most importantly, becoming a pain, anal and sissy slut is what Mistress Ayn wants for me as Her slaveboy and that is more than enough for me.

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.”

Venus in Furs – a book review

Monday, 09 November 2020 20:20
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I sheepishly admit that I have only recently read the iconic book Venus in Furs.  Written in 1870 by Leopold von Sacher-Masoch, the novella is a FemDom staple and in fact the term masochist originates from the author’s name.  I am not sure why I hadn’t read it before.  Maybe I balked because it was written so long ago.  Maybe I thought I already knew the story, but after learning a bit about Sacher-Masoch’s real life (he desperately wanted to be cuckolded by his wife), I decided to read it.  Of course I wanted the Sardax version with all the beautiful illustrations but it took a while to arrive, so I started one of the more readily available interpretations from the original German.

The book was a quick and relatively easy read.  The story, for those that are unfamiliar, is about a young man that is obsessed with thoughts of a dominant and cruel woman.  Like many fetishes, Severin’s was born in adolescence when an aunt, dressed in fur, harshly punished him and from that point forward his sexuality was intertwined with that experience.  He dreams of a woman he can call his own that would treat him in this manner.  Hopefully the incongruity in that statement is not lost on you, as it was Severin.

Enter Wanda.  After admiring Wanda from afar and transferring his fantasies onto her, the two eventually develop a relationship and Severin confides his desires.  This is the classic tale of be careful what you wish for and Wanda takes Severin on a physically and mentally cruel journey that he both hates and loves.  There is a quite a twist to the end of the story that I don’t want to give away – and it is worth reading to the end to observe the reckoning of fantasy versus reality.   The story is not salacious.  In fact the depictions of sex do not go beyond the occasional kiss or embrace.  Instead it’s a journey into mental and physical domination,  laced with obsession.

So I read the version by Fernanda Savage and right on the heels of finishing it the Sardax translation arrived.  I thumbed through the book, enjoying the gorgeous art.  Simply out of curiosity, just to see how Sardax’s interpretation compared to the other book, I read the first chapter and I was sucked right back in.  I can’t quite put My finger on why I liked the Sardax version so much more.  Maybe it was because the sentence structures were less archaic.  Maybe it was because Sardax really understands Femdom.  Regardless, it pulled Me back into the story and I enjoyed it even more the second time around.

If you haven’t read Venus in Furs, treat yourself and order the Sardax translation with illustrations.

 

 

 

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.

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