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@stayrandy

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Teach girls to prioritize feeling safe over being nice.

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Remember that when I’m kneeling in front of you and gagging and choking and looking up at you with teary eyes that I’m exactly where I want to be.
madsillustrated // "Stay Cool." (ft. @whoreocookiesnmilk)

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Wednesday night risqué fun … Popeye a tengerész (Popeye the Sailor) by artist Alexander Szekely
Queen // Fat Bottomed Girls
i’d rather be too woke than a fucking idiot
Chastity | 15 July 2026 | 1:07 p.m.
That’s the date and time I went back into chastity with a goal of reaching seven days in my cage before taking a break. It feels good to be back in my cage.
I love feeling the ring behind my balls and pushing the cage down onto my mostly erect cock always gets me excited to go back into chastity. That feeling when I reach down and tug at my cage is unique. I can’t access my joy stick and that in itself makes my balls ache and my cock strain against my cage a little.
History in chastity
No, this isn’t my first go-round with being caged. I entered chastity for the first time in June 2023 and I’ve been in and out of my cage ever since.
Yes, chastity is magnetic
As @askagni might say, once I put on a cock cage, a switch flipped in my brain. From that moment on my desire to be caged spread like a weed and my cage keeps drawing me back. It’s the true love-ache relationship.
So, here I am, caged again.
Why?
I’ve long been intrigued with Locktober, problem being I wouldn’t think of taking on the challenge until October was just days away.
Anyone who’s been in a cage knows long-term chastity requires discipline and endurance, and I wasn’t ready to take on that kind of challenge. I started Locktober last year, but I wasn’t physically or mentally prepared to go 31 days in chastity. I tapped out after 12 days because I was chafing pretty badly.
What’s next
With Locktober in mind, I’m going to train for it like a good boy. There are 78 days from today (July 15) to Sept 30. I’m going to do two 7-day lockups followed by a 10-day lockup then a 14-day lockup. Finally, I’m going to lock up for 21 days before starting Locktober.
With that plan, I’d be locked up 58 of them (20 days released). I’ll be well adjusted, physically. I should be in a pretty good head space, mentally, by then. I could fit another 14-day lockup in, if I choose to. That would put me at 72 days locked with six days of release. (TBH - Right now, 20 days released seems like too many. It would allow too much time to backslide, mentally.)
Long term
I have a bigger goal in mind than just Locktober, though. If I do well during that 31-day lockup, I might stay in chastity for No-No November and possibly Denied December.
Staying locked up for 92 days is quite a commitment. Throw in training, I’d be in chastity between 150 and 164 days. Would it be a leap to be permanently locked up from that point on?
Back to today …
I do enjoy priming my hormonal pump before I lock up. I find it jumpstarts my desire and dedication to chastity. I went into my tiny cage very horny after edging myself three times, the first two right to the edge of cumming. The first edge was right after shaving myself and before I put the base ring on. Then I edged again right after I put the ring on. Finally, I stroked myself hard right before I pushed the cage on and closed the lock. By then I was excited and ready to be caged.
Today, a shocking amount of precum was pushed out when I set the cage pins into the base ring, like a big squirt came out like clear toothpaste then enough precum seeped out to coat my balls and drip onto the floor. I still have a wet spot on my undies.
My final act of going into chastity again will come at 5 p.m. when I hand the keys over to my other. She’s a firm keyholder who will keep me on the edge of desire while staying locked in chastity.

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