This is a follow-on post from some experimenting I did with the Diamo locked behind a chastity cage, you can find that post here https://lovenselife.com/article/1693253347475

This post covers the main challenge I set

myself for the months of September and October.

For those that don’t know, Locktober is the month of October where many males and females experiment with long term chastity by remaining locked in a device for at least 31days. I have always wanted to attempt locktober myself, because the thought of being denied and teased and the eventual earned release has always appealed to me. But in my previous relationships and dynamics the timing never felt right, or something got in the way. So, this year I am pushing myself to do it and tick off one of those #lifegoals, but of course I decided to make it harder on myself which you will see.

For those who don’t know I am a BI switch with Daddy Dom and Sissy Sub tendencies, and during a recent relationship, my ex-partners alpha side sort of unlocked my Sissy Sub making me want to explorer it a bit more, for a couple of reasons. To make me a better Dom, by understanding the Sub side more and see if I could cope being a Sissy in a long-term relationship with a dominate woman if that was to happen in the future. I therefore decided to not only do Locktober, but Sissytember too, which involves being caged, plugged and receiving some form of feminisation for the month.

So combined I was looking at 61 days locked but bearing in mind I will sleep it comes down to about 62 Days in chastity with my diamo locked in place behind it. The original plan was to key hold myself, but at the last minute I found a beautiful Goddess to key hold for me, which we do via the Chaster app which also provides her with the option to reward and punish me from a distance and assign tasks to help me with my sub development and give her a little giggle from time to time.

The rules of the challenge is this

• No cumming during the lock duration

• I will remain locked at all times, with allowable unlocking once a week for cage Maintenance, cleaning and hygiene for a short period.

• I will remain plugged at all times, with exceptions for allowing physical training to take place and to allow recovery from some tasks.

• No boy clothes within the house and no boy underwear to be worn at any times only panties or nude

As I mentioned earlier, we are using ‘Chaster’ to handle the keyholding of the Cage as we live remote from one another, and the system helps to ensure I am well focused during my 62days+ locked up. To prevent myself from being penalised with more time in the cage, I must spin the wheel of misfortune 4 times a day, send my keyholder a verification picture to show I'm still caged and complete a minimum of 5 tasks a day from the task list.

The system only allows for up to 10 tasks to be chosen from, so we have an agreed list of tasks stored elsewhere that we pull from to keep the list of 10 fresh. 5 of the 10 tasks will be from the core training categories which are Anal, Oral, Bondage, feminisation, chores. These tasks are designed to help me be a better sissy and ready for anything, such as practicing sucking cock, licking pussy or be plugged. The other 5 tasks are chosen from a list to keep my Goddess happy and tease me in some way. So, if you see me posting links or grabbing links, please feel free to help me out with my task. and Goddess is quiet taken to the button which demands me to give her a Big ‘O’.

We welcome any suggestions for fun to do tasks as we have 62 days to fill and appreciate the help keeping it fresh.

I will continue to post to let you know how it goes keeping my Diamo on for the next 62 days and the trials and tribulations of chastity.

Have fun and stay kinky

Rectitude