My ex sub was very adventurous, but always had some reservations when it came to urethral sounding. Finally after a while I managed to convince him to try.

I got a nice sounding kit and good lube. Cooked him dinner with great wine. Finally when he was a bit tipsy I tied him up, arms above his head, legs spread wide. I left his cock alone while I focused on his ass. I fingered him for a good while, before I plugged him with the big plug and turned it on.

It was finally time to focus on his cock and balls. But the balls first. I slapped them bright red and the massaged them to ease the pain a bit. When I was satisfied with his whimpers, I took out the sounding kit.

I started with the smaller sound. His breathing hitched as it slit past the entrance, but soon it turned to moans. He was loving it. I started moving the sound up and down, then switched for a bigger one. He came hard on the third sound, his whole body trembling and shaking.

I toom the sounds out and game him a good post orgasm hand job while he was crying.