This subject came up on the old BooksieSilk site, and I saved my response. I just ran across this post, so I'll share it with you.
I have either witnessed or been involved in four instances relating to humiliation throughout my life that I can relate here. All of them influenced my writing in one way or another. I will list them in chronological order.
1) I was in third grade in a Catholic grammar school. Our teacher was a nun. One of the boys misbehaved—I don't remember how—and she punished him by placing a bow on his head. I don't recall the color, but I used a pink bow in "Tommy's Debasement" when Miss Richards invoked that flavorful punishment on the Tommy character.
In the real-life instance, the nun definitely was deriving pleasure with her employment of the bow. The poor, red-faced boy was forced to wear it for at least an hour, and the nun would occasionally walk over to him, stare at him, and smile. She definitely had a sadistic streak.
As an aside, she did not last the whole year in our school. We never heard what happened, and I always wondered if this instance had anything to do with her dismissal, or even if she was dismissed. Who knows, maybe she had a history of behavior such as that.
As for me, it was my first recollection of feeling titillated (for lack of a better word right now) over something involving humiliation. Like I say, it was third grade, so I would have been about eight years old. Like the nun, I was definitely deriving pleasure from the boy's humiliation and was ever so thankful that she chose him to humiliate and not me.
2) This one is by far the most humiliating scene I have ever witnessed. I was in either sixth or seventh grade, so I would have been around 11 or 12 years old, as was the boy whose experience I am about to describe.
It took place in the schoolyard. It was not a regular school day, so it was either on a weekend or during a school break. Nevertheless, there were several students of different ages playing in the yard, broken up into a few different groups. I remember someone yelling, "They're pantsing [name withheld to protect the innocent]!" I followed our group around the corner, and lo and behold there he was, already stripped to his tighty-whities. There were at least four (older) guys overpowering him, and he was screaming bloody murder and flailing away like there was no tomorrow. But he was no match for them, and they had him naked without any trouble. While he was being held back, one of them had the creative idea to bundle his clothes together, knot them and attach them to the flagpole and hoist them all the way up. They let him go, and I watched as he frantically pulled on the rope until he was able to retrieve his clothes. He then ran to a private spot (he was crying) to dress himself, and that was the end of that.
As for me, as you can well imagine I was enthralled with the whole scene. I remember thinking that I only wished I could have been there from the beginning. I watched from a distance, as I didn't want to get too close. I mean, I think they picked the poor guy out randomly—as far as I know he didn't do anything to deserve such a fate—he was a smaller guy, as was I, and I certainly didn't want to have the same experience! I got the hell out of there when it was over, just to be safe.
Some of you might be familiar with a scene in one of my stories (Roosevelt Humiliations) where the Blondie character's pants are hoisted to the top of a flagpole. Now you know where I got that inspiration.
3) This one involved me, and before you get your hopes up, I managed to avoid the humiliating fate that was intended for me.
I was either 12 or 13 years old and was at a sleepover with about six or seven other guys. I had stripped down to my underpants (yes, they were the dreaded tighty-whities) and was inside a sleeping bag on a bed. Out of the blue, one guy says, "Hey let's make Blondie (again, real name omitted to protect the innocent—me) walk around nude." A couple of people laughed, and he said, "I'm serious. Let's make Blondie walk around nude." Now I have no idea where that came from, but it was quite apparent that this guy wanted to see exactly that. He started walking over to me and I don't remember, but either one or two other guys were with him. Fortunately for me the rest of the group wanted none of it.
One of them said they should throw me out in the snow naked (it was wintertime in upstate Washington, where I lived at the time). In any case, the (two or three) guys started pulling on my sleeping bag in an effort to get me out. I fought like hell and hung onto the bag for dear life, and they eventually gave up, much to my relief. My heart was beating a mile a minute.
I used the scenario in my story "Stripped by Friends," but of course the Blondie character suffered a much worse fate than I did. I can tell you that the sister of the guy who lived there was in the next room, as in the story. I don't remember if she had a friend over, as she did in the fictitious story. I want to say she heard the commotion and came into the room, but I can't remember for sure.
4) A simple stripping at a pool here. I was a high school freshman (14 years old), and we were swimming in P.E. I heard some yelling and a few of the seniors (juniors, maybe) had stripped the trunks off one of the small freshmen. One guy had him in a bear hug, and he lifted him up a couple of times, exposing his hairless, prepubescent package. Funny, I can still picture it to this day. When he let him go the freshman was swimming frantically back and forth as they were throwing his trunks around, playing keep-away. It lasted just a couple of minutes before the laughing seniors let him have his trunks.
Again, it was another pleasurable experience for me, and again, I was ever so thankful I wasn't the victim.
So there you have it. I guess my attraction to humiliation and my inspiration to write about it may have started at the ripe young age of eight. Little did I know then that a nun's act of applying a pretty bow on an unfortunate boy's head was the beginning of a predilection that would bring me enjoyment for many years to come.