Go milk yourself

My wife continues to become more and more taken with the world of cuckolding (hold your requests - no pictures allowed) as the cocks get larger and attached to more men, some whose name we actually hear before she's impaled on him.

On the other side, George is no longer permitted even to masturbate. This makes coming here really hard (if you know what I mean). But I'm trying to be a good wimp and obey so I don't find a CB6000 in my punishment corner someday.

I am allowed to milk myself. I've tried this with a toothbrush handle (a tool selected by my wife and her fuck of the day) without success. I pushed hard on what I believe is my prostate, but cannot get it to "give it up" and release the semen.

Does anyone suggest a better tool? She's told me if I want it, I have to do it myself. She's not helping.

Can anyone suggest a good method?
What should I expect as far as feelings? I don't mean an orgasm, but how do I know when I hit the prostate and that I'm making progress?

A cock to die for (if you're a cat) and that's hard!

When it's limpy, it's even more wimpy.

George Nobush
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try uretherail sounds, they are long steel rods used to dialate the male pee tube. they can reach down to the prostate and massage it into milking from the inside. I have 2 different type, and have enjoyed success with both.
jackie

TBQH I wouldn't bother if I were you. needle dick

but if you do bother, then get on your knees and insert your longest finger into your anus keeping it downwards toward your penis, at about your second knuckle, you will feel a "lump" which is your prostate, this is the region you are aiming for, but massage it slowly and for a long time, and remember, "milking" is not the same as an orgasm.

I think you would be better off getting another sissy to suck your tiny cock dry while your mistress and her boyfriend howl with laughing at you both is favourite tho.

It shouldn't take a long time to milk your prostate...I've never done it to myself but, I've had it done to me.....as soon as you push on it, it should start to flow but, it is true that it's not like cumming....it's like you get ripped-off....25% of what an orgasm normally feels like.

Try a D-cell Mag light with a condom on it.

Works everytime for me

omfg chastized one