I’m not sure what to do. After three years of wearing my Jailbird, it tends to slip off when I sit or get ready for bed. I suspect that losing 35 lbs recently might be part of the reason. My face, wrists, and even feet have been getting smaller too. Plus, aging seems to be shrinking everything down there as well. I’ve already sent my Jailbird back to MM three times—once to reduce the ring size (which increased the gap) and had them drill it out for the security screw. Having worn this thing so long now feels like being on the honor system again was good relief. The constant pull-down pressure from the Jailbird made me feel like I needed to pee constantly, plus there was always the hassle of cleaning myself afterward. And let’s not forget that occasional burning sensation in my scrotum.
Still, without it, I feel quite exposed. I want to keep wearing it but know it could slip out again. After two months without an orgasm, my penis seems ready to retreat into my body, which creates more room inside the ring for now. For the moment, I’m winging it, though the urge to masturbate or edge and go just one stroke too far is growing stronger. I plan to hold off until New Year’s Eve to see if my wife grants me permission to orgasm. If she does, I’ll take a break until about a month before Valentine’s Day to lock up again and test how it goes. However, since I’m still losing weight, I might need to wait until my diet is finished in roughly 10 months. I have another 75 lbs to lose to reach my optimal weight, but that would mean giving up many of the foods I love forever—and honestly, I’d rather give up a few years of life than miss out on cheeseburgers and pizza with beer!:)