This patient has been concerned about having anything in his ass besides my finger but during this session I convinced him to at least try the Anal Intruder Cockring. It's a device that's basically a rubber butt-plug with a cockring attached. When it's working properly, any cock movement applies stimulation to the prostate.
Unfortunately he wasn't ready for something that large yet so I used my finger to manually stimulate his prostate while I milked his cock with my other hand. He said he came earlier today so I was surprised how much cum he produced.