Tag Archives: chastity

Trials and tribulations of a chastity slave – Installment #8

Saturday, 06 April 2019 10:31
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Installment #8 – When “playing” with chastity became a “lifestyle” of chastity. – by slaveboy

Many men and some couples “play” with chastity.  As a male, it was a fun way to fantasize that a Dominant Woman was in control of my cock and restricting me from getting an erection or orgasming.  i would put on the cage for a few minutes, an hour, or even a day, but then remove it when i wanted and revert to my familiar masturbation practices.

Couples often use chastity as a way to spice up their sex life, with the female taking control and the male submissive.  It is a fun way to spend a day together, or a weekend, or for the dominant partner to threaten longer chastity sentences.

Yet, at some point my “playing” with chastity became living a chastity “lifestyle.”  Once Mistress Ayn became my Keyholder and took over control of Her cock with Her chastity cage, my world was turned upside down, but in a good way.

Now i am permitted release from Her chastity cage for a few minutes, or an hour, or rarely a full day.  i never know when this permission will be granted.  Then, it is back to normal for me – back in Her cage, often without an orgasm and very rarely after a real orgasm.

i am unsure when this transformation actually occurred.  When did i realize that W/we were not “playing” with chastity but it was now a lifestyle?  Each month i pay my keyholder fee, as a tribute for the attention that Mistress Ayn gives me as Her chaste slave.  Each month there is no discussion of ending this relationship, nor do i intend to bring up.  W/we do not have a set ending – not after a month, or six months, or a year.  She does not refer to my chastity as permanent chastity but prefers indefinite chastity.

Indefinite, as in a lifestyle, suits me just fine.  It brings me closer to my desire for a female-led relationship, a life where i do not control my cock, and a re-orientation of my attitude toward pleasing a Woman, my Mistress, rather than satisfying my selfish carnal desires.  This seems to work for me right now in my life, even though i am not fully aware of when this transformation actually occurred.

Trials and tribulations of a chastity slave – Installment 7

Saturday, 30 March 2019 19:32
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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

Thursday, 07 March 2019 11:51
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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

Thursday, 28 February 2019 11:11
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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

Friday, 22 February 2019 10:55
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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.

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