Embarrassing experiences are some of the most vividly remembered... Here are some of mine:
Diaper-related
• At the age of 8 or so, my father (who had strange ideas about discipline) told me I would be diapered in full view of the rest of my family. I was helpless on the floor with my pants off and my penis and scrotum in full view of everyone, while he took his time using a powder puff to powder me, and putting me in a diaper. My brother and sister were howling with laughter.
Spanking-related
• Between the ages of 6 and 9, I'd get a half hour of corner time after a bare-bottomed spanking, and the half hour was almost always pants-down. I think I felt more embarrassed having my pants down than if I'd just been naked. It seemed to make a point of shaming me by everyone getting to see my hips and penis, in particular.
Dad even ordered me to stand out some distance from the wall, arms at my sides, so I couldn't hide my genitals. Family members were free to walk in and out of the living room, while I was standing there. My older sister thought it was hilarious.
I only recall one instance of a neighbor coming over and seeing me like that, but I never forgot her smile and smug advice... "Well, you be sure to mind your mom and dad, so they don't have to do this again."
As a child, Medfet-related:
• There was a strange nurse who liked to pull down my pants and underwear all the way to my knees for shots, and then keep them down for inexplicably long periods. Even as a kid, I wondered why my little cock and balls had to be out (she could have just pulled down my pants in back, for the shot), and why it took her so long to tell me I could (finally) pull them up. Later on, I realized she was enjoying the view.
As an adult, Medfet-related
• A few years ago, an elderly male doctor telling me to strip entirely for my physical (that hadn't happened since I was a child), and when it was time for the genital exam, taking his sweet time rolling and stretching my cock, and cupping, smoothing, and stretching my scrotum and probing my balls.
As an adult, massage-related
•• One evening, a massage therapist was on duty alone, and she kept leaving me completely undraped face-down on one of her tables, with the door to that room left open, while she went to the front to admit walk-ins. Two of those walk-ins — sent back to wait in another massage room — were young ladies who burst out laughing when they passed my doorway and saw me bare-ass naked on the table. I didn't dare look up... It was a small town and I probably knew them both.
•• Two 'massage therapists' who turned out to be staffing a massage parlor (it was advertised as a legit massage clinic) had instructed me to take off everything, cover myself with a thick towel, and wait face-down on their table, while they went to get the oil. I did that.
After they came back in the room, they spent about five minutes clumsily massaging my shoulders; and then one of them pulled my towel down past my bare buttocks, leaving me completely naked. I wasn't expecting that. When I pulled the towel back up, one of the ladies laughed, and asked if I was cold. When I admitted that I wasn't, she said, "Just relax, then..." and slid the towel back off.
Well, it wasn't all one-sided...by the time they had me face-up and were stroking my oiled cock, both of these slender women had stripped down to their panties (beautiful boobs and dark nipples), and one of them was pulling her panties down past her dark bush as she asked if I wanted "full service." I didn't...but at least I got to see almost as much of them as they did of me. Their massage skills were second-rate, but they had wonderful bodies, and to this day I fantasize about saying 'yes' to full service and fucking the one who asked, from behind, while the other one watched.
But then, they probably wouldn't have found that embarrassing...