Category Archives: Chastity chronicles

Trials and tribulations of a chastity slave – Installment 7

Installment #7 – The “Evils” of ED Drugs – by slaveboy

Many men are aware (and an increasing number of women) that there are erectile dysfunction (ED) drugs on the market: Viagra, Cialis, and more.  Mistress Ayn enjoys ordering me to take one of these ED drugs since it does shorten the time for me to become erect after removal of Mistress’s chastity cage and the time i can remain erect.

Yet, Mistress Ayn’s enjoyment is in how She decides to use this medication – not exactly as prescribed.  Rather, She orders me to take the ED pill and then edge myself for a pre-determined length of time.  Since it has been so long since my last ordered edging session, i am erect within a few minutes – the ED pill has its effect.  But, rather than “finishing” and orgasming, Mistress Ayn orders me to stop before orgasm and place Her cock back into Her chastity cage.

This is where the “evils” of the ED pill start to become evident.  It is difficult to get a fully erect cock back into a small chastity cage.  But, as an obedient slave, i comply.

Then, the “evils” of the ED pill continue.  My ED pill “works” for a few days, but i am typically in chastity after the edging session.  Thus, any miniscule arousal is frustrating and painful as Mistress’s cage restricts me from becoming erect.  Mistress Ayn knows this, obviously, and often orders me to watch porn, further aggregating the frustration and painfulness and exacerbating the “evils” of the ED pill.

What is a medical marvel for many men and a wonder drug that enhances most relationships is a brilliantly evil and sadistic way for Mistress Ayn to further control me and remind me that She indeed is in charge of me and Her cock.  i am so appreciative of learning the lesson of the “evils” of the ED pill and having Mistress Ayn control my life, which includes Her cock.

Trials and tribulations of a chastity slave. Installment #6

Installment #6 – A Memorable Super Bowl Sunday – by slaveboy

Most of America’s attention was on Super Bowl LIII. i did favor the LA Rams, born in LA, and my current hometown team has lost repeatedly to the New England Patriots, so animosity against that team. Mistress Ayn decided Super Bowl Sunday was a key day in my chastity sentence. Anxious for some release and possibly the first orgasm in 2019, i jokingly suggested that the Super Bowl was moved up to Wednesday – She knew better – and then on Saturday i informed Mistress Ayn that it was Sunday in Australia – again, She stood fast.

Finally, on Super Bowl Sunday i was ordered to remove the chastity cage, not wear underwear, and take an ED pill. This caused me to be erect most of the day. Mistress Ayn also told me to repeatedly edge during the day and “make Me proud.” i took this to mean – edge often and for longer periods of time, as She has ordered me to do in the past. i achieved five edges during the day and each for a longer period – 10, 15, 20, 25, and finally 30 minutes. It was extremely difficult to not “go over the edge” as i had not had an orgasm for two weeks and no “real” orgasm for five weeks.

Mistress Ayn explained – if “your” Rams win, you can orgasm but ruin it. If the Patriots win, you can have a “real” orgasm. i also knew it was implied to “recycle” my discharge.

Watching the game was difficult since i wanted to cheer for my Rams, but also wanted a real orgasm. Despite a low-scoring (read: boring) game, the Patriots did win. i did get my “real” orgasm – a huge load, all recycled – despite my sadness at the outcome of the game.

Trials and tribulations of a chastity slave. Installment #5

Installment #5 – A Day of Freedom and of Control and Pain

i had mixed feelings about an upcoming supervised release – I enjoy being under Mistress Ayn’s control in chastity but desperate for a release.

After two weeks of chastity, the freedom was quite nice – it all starts out nice.  BUT, there is always a pain element too.  Ordered to wear pink panties was agonizing as they rubbed against Her now unencumbered cock and balls, excruciating stimulation.  Plus, i was ordered to take a Cialis.  i was so intensely aroused.  i followed Mistress Ayn’s orders to watch porn during the day but no touching.  The erection was very hard and caused me to shake with desire for relief.  i wanted to touch myself so badly but was obedient.

After a very long day, evening arrived and the next order = an orgasm.  Ah, but not so fast slaveboy, a RUINED orgasm.  Yikes!!!  And, slapping Your balls – hard, as ordered – as i came.  Double yikes!!!

As ordered, there was photographic evidence on Twitter of the discharge before i licked up every drop.

Despite the freedom, watching porn, and an orgasm (albeit ruined and with painful ball slaps), i felt little pleasure or satisfaction, and it was back in the cage.  The ED pill continues to stimulate for days, so the chastity restriction was particularly painful. i craved an orgasm, a real orgasm.

So many questions as i tried to sleep: How long in chastity this time?  Will i EVER get a real orgasm in 2019? Is there anything that i would not do if ordered by Mistress Ayn?  How could the pleasure of a release be made even more painful and unsatisfying?   Will i actually survive being Mistress Ayn’s chaste slave?  Why do i have just a huge smile on my face (hint: i have pleased my Mistress, which makes it all worth it)?

 

Trials and tribulations of a chastity slave – Installment #4

Chronicles of chaste slave – #4 – The emotional transformation and control – by slaveboy

i am becoming aware that every command has its own powerful control over me. While Mistress Ayn’s orders may sound sweet and caring (chastity freedom), Her commands have a powerful and sadistic edge (no touching, no orgasms). Whether ordered to orgasm multiple times throughout the day or within a limited time upon command, to orgasm but ruin it, to edge for longer periods but not orgasm, to remain in chastity indefinitely, or to be released from chastity but refrain from any stroking.

Paradoxically i desperately want to orgasm and feel pleasure, yet also desire the comfort and security of chastity (realizing that I have spent 98% during the past few months in chastity – that has become my “new normal”). This is both an exhilarating and a frightening life existence as Mistress Ayn’s chaste slave. She has my head spinning and my emotions in chaos and the only option i consider is complete surrender to Her, to trust Her, and obediently follow Her commands.

My emotions swing widely. There is the excitement at experiencing this new chapter in the journey of my life and a sense of correctness with having Mistress Ayn in complete control of Her cock, waking each day and reminded throughout the day that Her cock is securely caged. There also is a growing fear of not fully understanding what i have gotten myself into and an utter helplessness of loyally following Mistress Ayn’s orders (all while i have the key but cannot convince myself to playfully abuse Her cock during maintenance times or release Her cock unless instructed).

i also have been pondering my lesson learned — never, ever, ever displease your Mistress.  i know Mistress Ayn is strict with me since that is how i am learning and the only way to undo all those years of control, power, and a lack of total respect for Women. i need the discipline — wish Mistress Ayn could see it in person — and the control She exerts. i wish i could express how truly happy i am with Mistress Ayn as my Keyholder. i am thriving being Her slaveboy – both in person at the Femdom Mansion and virtually via emailed commands and chastity sentences.

Trials and tribulations of a chastity slave. Installment #3

Installment #3 – The holidays as Mistress Ayn’s chaste slave – by slaveboy

To celebrate the holidays, Mistress Ayn permitted me out of chastity on Christmas Eve and Day but not allowed to touch Her cock – two days of freedom but not really. i could feel Her cock and balls dangle freely but that only made the urge to stroke more intense. This was a true test of my obedience to Mistress Ayn. After Christmas, back in the chastity cage.

On New Year’s Eve, after two weeks of nearly consistent chastity, i was permitted a one-hour edging session near the stroke of midnight. While i appreciated the opportunity for release, i was ready to orgasm almost immediately but knew to not orgasm early. A full 60 minutes later, i “recycled” the discharge from my powerful orgasm and Her cock was back in Her cage to greet the New Year.

Will 2019 be any different as Mistress Ayn’s chaste slave? In Her New Year’s Eve email, Mistress Ayn said: “Have a nice powerful orgasm, knowing that it is the last one of 2018 and possibly the last one ever.” “Who knows what the New Year will bring?” “I’m just laughing thinking about how much you are going to want the next orgasm – which may never happen.” “The New Year’s Eve orgasm may be your last orgasm ever.” These words resonate with me each day in 2019.

It is clear that being Mistress Ayn’s chaste slave requires a deeper commitment than i first imagined, but one i am willing to make. While Mistress Ayn was a bit hesitant at being my Keyholder, i did not expect Her to become so comfortable and creative in this role. Chastity control appears to be something long term for Mistress Ayn and She enjoys using the term “indefinite chastity.” Her control through chastity is requiring me to better integrate chastity, mentally and physically, into my otherwise vanilla life.

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