Chastity and orgasm denial discussion

One of my former pantyboys has modified his underwear (his idea/fetish, not mine) in a way that would surprise most sissies. He gets the crotch cut out so his scrotum hangs down beneath the fabric, and then he keeps his penis facing upward against his stomach. He enjoys having his testicles tugged on or things hung from them, etc., but is very careful with his cock, which helps explain how this setup came about. A simple ring or a 3-ring circus works well for him in this position, and often does so. However, he’s searching for a chastity device that will let him keep his penis pointed up - while still being able to direct it downwards when urinating. He isn’t doing this under the control of a Mistress, so can decide on this method independently. Any suggestions? M