Olive’s First Time in Full Chastity

Desperate chastity slut
My little Slave Olive is all grown up now. After purchasing his first chastity device he first placed a plastic numbered lock to secure his device over the weekend… by my instruction of course. He then moved on to being locked up with the padlock but he kept the keys. Again by my direction he would stay locked up for up to a week or more at a time with occasional spot checks via Whatsapp to make sure he wasn’t unlocked when he shouldn’t be. Each time he was so nervous about embarking on a new baby step of a milestone so I decided to throw him in the deep end to finally get it over with. I demanded that he locked himself up and send me his keys.

It took him nearly a week to actually do it. I was not pleased by this of course. Unfortunately I had to remind him that what I say goes and there’s no arguing with Mistress. No excuses, just send me the keys. I’m happy to report that I did receive the keys yesterday but I was not happy with the note he left me. Here’s Slave Olive’s account on his first time in full chastity, his fetish faux pas and how he made Mistress happy once again.

Slave Olive posts the keys to his chastity device

Olive Locked in Chastity

Olive Locked in Chastity

I am currently locked in my chastity device and have been so for the last 5 days. Mistress Selena has the only keys, and I don’t know when I will receive them back.

At first, I was reluctant to send the keys to the padlock on my chastity device to Mistress Selena, as I knew that after I had done so, I would be completely at her mercy. Eventually Mistress Selena demanded that I lock myself up, and post off the keys.

I sent off the keys taped to a piece of paper in a padded envelope. On the piece of paper I was stupid and selfish enough to write, “Please don’t keep them too long Miss.”

Mistress received the keys to my device yesterday, and rightly decided I needed to be punished for my selfishness. My chastity and frustration is what makes Mistress happy. My own pleasure is not important. I have sacrificed all my pleasure and orgasms, so that Mistress Selena’s own pleasure is improved. This is why my stupid and ill thought out message on the paper my keys were attached to was so pathetic and selfish.

Mistress told me to insert my butt plug and torment myself by looking at kinky and popular for one hour. I was then told to take a picture of my device and locked cock dribbling pre cum and post it on Fetlife. After this task was done, Mistress informed me that I now needed to be creative and come up with my own ways of punishing myself.

Olive slamming his balls in a drawer

Olive slamming his balls in a drawer

I first wrote “MISTRESS SELENA’S CHASTITY WORM” on my leg, then “DESPERATE SLUT” on the other leg and sent her pics. I slammed and squashed my balls in a drawer, took a pic and sent it to Mistress. I made a video of myself whacking my balls. I got my chastity device out by a window in my flat. I then also got my chastity device out and on show in the communal area of my building. I don’t know if I was seen by anyone. I then got dressed in a bra and panties and took a pic. Mistress appeared satisfied and sent me off to bed, telling me I was forgiven.

So, here I now am, locked and desperate, as Mistress likes me, writing my report, trying to be a good chastity slave.


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About Slave Olive

Slave Olive came to Mistress Selena first to gather information about male chastity. He felt so comfortable with the way Mistress patiently explained how to get the best out of chastity play that he immediately purchased his first chastity device and locked himself in. He has been under Mistress Selena's control ever since.

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