Lilith,
Have you ever put a man a gates of hell ? It is series of 5 or 7 steels rings connected with a leather strap. The lower one is used like standard cock ring it goes around the cock and balls, the rest go around the shaft. As you get harder the rings squeeze the shaft. Besides staying very hard it is not easy to cum while wearing it. A used to have one an ex bought for me. She loved to "make " wear it. SHe would tie a rope around the leather strap and use it as leash, .she torment me by keeping me hard like that for hours. She like to tie me to a chair and twirl the rope in circle it would make me hump the air like a dog in heat trying to get off. The few times I did cum while wearing it ...OH MY GOD it was so intense !!!
Sorry I do not the pictures of me in it any longer.

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Sailing Fool