Here is a tale of some humiliation play a friend and I did a long time ago.
In the summer of 1995, a dominant friend and I went to an early dinner at a pizza place in Alexandria, VA. This was back when I was still very new in the scene. After dinner, she drove me (in her car, a toyata) into Georgetown and we visited an adult toy store called the Pleasure Chest.
She had me carry various dildos and other toys through the store, trying to humiliate me. I managed to survive that. So after she buys some items, we go to her car which is parked outside on the sidewalk. After we get in the car, instead of starting the engine, she opens the bag, hands me the dildo, and tells me to start sucking on it.
At this point, I don't think I had ever sucked on a dildo before and although I had some dildo fantasies, I was very cautious and aprehensive about bi-erotic stuff. Its light out and people are walking by on the sidewalk and I'm sitting in the passenger seat trying to pretend I'm invisible while sucking on a 9" black dildo.
Then a pedestrian starts knocking on my window. I pretend I'm invisible. I don't look at the pedestrian or otherwise react. My friend orders me to open the window. So I roll down the window. The pedestrian asks if we're leaving the space. He wanted to move his car (parked down the street I guess) into our space. I pretend I'm invisible while I suck on my dildo as my dominant friend answers him. She tells him that yes, we're leaving the space. He leaves. I roll up the window while wondering what on earth he was thinking about us.
As she drives into the street, she tells me to drop my pants around my ankles and to keep sucking. She orders me to masturbate and keep on sucking. She orders me to look at various pedestrians and other drivers. She tells me that if I cum without permission, she'll stop at the nearest street corner and shove me out of the car.
I'm crying at this point. Hot tears streaking down my cheeks as I continue to suck on the black dildo in my mouth and pull on my hard cock. My glasses are steamed up by the heat my face is generating. After driving for ten minutes, she pulls in a space along the street behind a toursit bus. She tells me to look to the right, I see the White House. She orders me to smile for the Secret Service cameras and the tourists. I'm cuming all over myself. She tells me I came without permission. But she decides to be lenient and not shove me out of the car after listening to me beg.
Most intensely felt humiliation scene of my life. I've done things since then that are considered more extreme in some ways, but this generated the most intense feelings and the most crying.