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October 2018
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Parole Mistress And The Parolee Slave

International Male Chastity Day

Parole Mistress has her work cut out for her . Since January 14th is the International Male Chastity Day, it may be very possible to pass the penis of this tiny cock celebrating 60 days of chastity training and orgasm denial. Nothing is mentioned here if the slave gets release either. Maybe it would be best  to set up a “pass the little locked penis” session for slave auction with him that day.  We  Mistresses could take turns to interrogate him to find out how well he could do being their submissive chastity slave house boy.

Parole Mistress And The Parolee Slave: Mistress Cassandra 1-800-730-7164

The Interrogation Material

*Locked 24/7 in chastity cage (currently on 60 days orgasm denial during training period)
*Will pay to serve Mistresses and Princesses
*Submissive, obedient, and docile
*Proficient in all housework, cooking, vacuuming, dusting, cleaning of sex toys
*Washes cars, mows yards, cleans pools
*Performs cunnilingus, fellatio, ass licking on demand (good luck with this option) , eagerly swallows all cum from male hosts
*Provides pampering and spoiling of Mistresses and Princesses, back massages, foot massages, toe licking
*Tease him, spank him, whip him, make him scream and squirm with some pegging, small cock verbal humiliation, cuckolding
*Trained to sleep at night in an animal cage, wears collar and leash during the day

All of this can and will be used to grill this slave for the convenience of the pass the penis Mistresses involved.

His Crime

How did this slave end up with such a severe parole sentence? That is to follow , but I will tell you he touched a Victoria Secret sales associate inappropriately and was then sentenced to 2 years of 24/7 chastity. I am the parole officer, and I hold the key to the cock lock.
I will let this slave comment on this blog post on how he cannot find a job because he is a pervert. But he did find one job for Ms Olivia and Ms Delia at “Wit’s End”, a nice little dungeon working as a cocksucker and splooge boy wearing his panty collection shown above.

Mistress Cassandra 1-800-730-7164



6 comments to Parole Mistress And The Parolee Slave

  • Ecock

    Dear Mistress,
    Forgive me for asking, I am wondering though, how does someone actually acquire this type of a job?

  • Prisoner Boy

    Thank you Parole Mistress Cassandra for your wisdom and guidance. I very much regret groping that sales girls butt. She was wearing a little mini-skirt and I just couldn’t help myself. I tried to apologize to her but she did not accept it and said I got what I deserved. A 2 year sentence in chastity. Today is Day 44. There are more than 22 months to go! I am really, really hoping I can get some time off for good behavior. Because of my sentence for being a pervert, it was difficult finding a job, no one wanted to hire me, but I wanted to show my parole Mistress that I could be a worthy and productive member of society, so I got a probationary job with Misstress Olivia and Mistress Delia at their dungeon, At Wit’s End, as a cleaning boy and cocksucker. I am thankful to them for hiring me. I still have trouble swallowing jizz without gagging on it. But I am learning to accept it. And that isn’t even the worst part. The worst part is watching Mistresses and Princesses and their well endowed studs enjoying hot sex, If I stop to watch too long I get ordered to go back to work cleaning until I am summoned. It is my honor to serve and worship Mistresses to show that I am a good boy. Thank You Parole Mistress Cassandra!

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