62 days of diamo

[re****]

This is the start of a sequence of journal entries I posted on the old site lovenselife website a couple of years back and I thought the community might enjoy my trials and tribulations. I intend to post a new journal entry each Monday as I did back when I did this experiment.
For those that don't know a diamo is a vibrating remote control cock ring. It sits at the base of your cock and balls and has an extended vibrating part which can sit between your balls or butt. I did some experimenting and found i fit the diamo behind my chastity cage and lock it in place. I did some short trials of it being locked on during the summer and then devised the following challenge.

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 dominant 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 Maintenace,
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 (now many more) 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 pegged. The other 5 tasks are chosen from a list to keep my Goddess happy and tease
me in some way and Goddess is quiet taken to the button which demands me to give her a Big ‘O’.

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

[Do****]

This is a great post for the subbies to read about experiences of Chastity! It’s amazing fun, for the Domme too! I have some locked away for Locktober and it’s fabulous!

[Do****]

Series of posts………

(If only the links in them worked in the app)

Use the search bar at the top of the forum (pull down to see it) and search for 62 days to find the next post, entitled week one

[re****]

3 hours ago, DommeDelight said:

This is a great post for the subbies to read about experiences of Chastity! It’s amazing fun, for the Domme too! I have some locked away for Locktober and it’s fabulous!

Thank you 😊 it was certainly an interesting and revealing part of my. I learned a lot from my experiences and I am happy to share and help others. Two years on I am certainly different being more Dom and more sub as I switch and still practice chastity every locktober with chaster and the great community there as we enter the challenges and have fun together 🫶 I wish you and your lockies a great locktober.

I just posted this week's entry and should be approved shortly

Edited October 13, 2025 by rectitude