Too big

The urethral tube which ends in a bulb is impossible for me to get into my urethra. I've tried several times with silicone lube, but no luck.

I'm not surprised. I guess that I will need to get a training sound that will expand my piss hole.

Suggestions?

So, I ordered this

I'm kind of scared, but excited, of course. I've done a bit of urethral play but we'll see.

Gone fishin'

Well, I'm about 3 weeks into this period of chastity and my libido seems to be on vacation. It's funny; just a few days ago I was waking up at 4 AM with a nice erection straining against my cage. Just a glance at a picture of a shirtless guy would "awaken something deep inside."

I'm sure that this, too, will pass. I hope so.

Should I get a keyholder?

I'm good at keeping myself locked but I'm still in control. I'm thinking that giving up control would be the next step and a turn on.

What do you think?

Would you be interested in being my keyholder?

Inadvertant Prostrate Massage

It's been a week since my last orgasm, not particularly long, but I guess long enough.

I was "taking a dump" and just after I finished my "business" I felt a vague sensation like I was urinating. I stood up and saw a long line of precum/cum draining from my locked cock. It wasn't a pleasurable experience--I didn't feel much of anything.

Another ruined orgasm.

Wet myself

I'm wearing my Jailbird today, the first time in maybe a month or more. I wore my Holy Trainer for a few days previously and was able to pee standing up. I went to the mens room a few times today and the stall was busy both times. I was able to pee at the urinal without problem before but this time...

I thought everything went well but then as I was walking out of the mens room, I felt a bit "wet." I looked down to see a wet spot down my left leg about 12 inches long! Nobody saw and now I'm trying to dry myself out.

Just part of the humiliation of chastity.

Deflation

After an approximately two week lockup, I removed my Jailbird last Friday night. I had gone out to dinner (Chinese) and it didn't sit well. I could barely keep my eyes open that night and didn't even try to get hard or cum.

The next morning, I awoke and thought I would clean out the pipes. I would concentrate really hard and my cock would get half way there but then soften again. After about half an hour, I gave up.

Finally, Saturday night I was able to get a decent erection and cum. Sunday was another effort but success and Monday, no problem.

"Use it or lose it?" I think it's cumming back, so to speak. I'm planning to take at least a week off from chastity anyway. I guess it's time to build that muscle memory.