Yes, several times.

One Mistress, within the first 10 minutes of our session, rammed a vibrator against my cock while she pressed Her Pussy against it and commanded “I cum before you, get it?” I couldn’t…

Another time an incredible Mistress yanked on my neck collar leash tightly, pulling me up to her naked triangular heaven and instructed me to kiss her inner thigh, roughly 3” away from her pussy, while she quickly and expertly masturbated. This scene was so hot. I still think about it.

Another session with a Mistress who I have seen for many years instructed me to jerk off while she vibrated herself to orgasm. We laid on our backs in opposite directions. This experience was a little unusual for me at the time. I think she was trying to burn off a little excess energy from he life outside of the dungeon.