A Million Dollar Humiliation

Story Categories:

Story Tags:

Views: 5,852 | Likes: +32

Why did I allow the rich man to humiliate me? Because he paid me a million dollars for the privilege. Also I wanted it. I would have never said yes unless I wanted it. If I didn’t, then there wouldn’t be any amount of money in the world.

We started in his bedroom. He ran his fingers through my waist length red hair. Then he tied it into a ponytail with a common rubber band. I only used silk or satin products before that. As I knelt before him, my hands tied behind my back, he wrapped my hair around his dick and used it to jerk himself off.

“It was your beautiful red hair that first attracted me to you,” he said, bringing himself to pleasure, “and I am looking forward to taking it from you.”

Oh, yeah, I knew that, after he finished pleasuring himself with my hair, even using it to wipe the cum off his dick like it was a paper towel, he’d break out the scissors and start cutting. It was part of our initial negotiation. He held my ponytail, which was fully saturated with his juices, tight as he sawed it off. My remaining hair spring free and hung around my face in ragged clumps. Then he dragged me by the arm to his bathroom. He dropped my ponytail in one of his trashcans on the way there. Treating it like common garbage. He knelt me down on the cold tile floor of his bathroom. Then he took out the clippers. As I screamed and cried, with my pussy dripping wet, he buzzed my hair down to nothing. Faint red stubble covering my pale scalp.

“I knew that you were vain, but I had no idea how vain,” he said, putting down the clippers once he finished and rubbing my buzzed head.

My eyes still full of tears, I said, “Why did you shave my head, sir? I thought that you were just going to take the ponytail.”

“Don’t you want to be punished? Isn’t that why you agreed to today? Then why wouldn’t I shave your head? In fact, you should be begging me to shave you smooth head to toe with a razor. As punishment for your vanity.”

Knowing that he was right, so right, I begged him to shave me smooth, from head to toe, with a razor. He obliged. After he lathered me up, slapping the shaving cream on my scalp, he used a BIC to shave my head smooth. Then he did my eyebrows. And, even though I came to him waxed, he lathered up my pussy and gave that a once over. Once he finished wiping me off with a soft grey towel, he made me look in the mirror. Really look at what I had become. I screamed and cried at the sight of me, bald and browless, looking like Gollum. However, when he stuck a finger up my cunt, he found it wet and willing. For a while, he teased me, bringing me close to climax, but stopped when I was just about to go over the edge. Much to my horror, he then locked me into a sinister looking chastity belt. Once that was secure, he unbound my hands.

“There’s a grey sweatsuit and black Crocs waiting for you in the closet,” he said, putting on a elegant black suit, “Put them on.”

After I dressed in that hideous outfit, baggy and oversized, probably to hide the chastity belt, he brought me to his vast garage. I needed to get into the trunk of a black car. He blindfolded me first. When we arrived at our destination, a bumpy hour later, he kept the blindfold on until we were inside. I found a nurse, with a little white cap on her shiny bald head, waiting for us in front of an old-fashioned ECT machine. He helped her wrestle me to the table and strap me in. I remember staring up at him, the bit to kept me from biting my tongue in my mouth, as the nurse flipped the switch.

I woke up in my apartment in a groggy haze. Still wearing that ugly gray sweatsuit and those stupid black Crocs. And that chastity belt. Whoever brought me home helpfully left the key on my nightstand though. They also put my phone nearby. They even plugged it into the charger. I checked my bank account, and my promised million was there. Satisfied, I went to go unlock the chastity belt and see what other indignities were done to my body during in the period of ECT fog. I only found a single bandage on the back of my bald head. When I pulled it off, it revealed a tattoo saying “Former Rapunzel Cured Of Her Vanity” in bold black lettering. We had discussed tattooing, but I never imagined that he’d make such a cruel choice for me. I prepared to unlock myself and masturbate furious over what he did to me, only to get a text message from the rich man. It offered me 5 million more dollars if I kept on the chastity belt and kept my head shaved for the next year. I would also not be allowed to wear make-up or any flattering clothing.

Oh, I said, putting down the key. Then I texted him back “Will do, sir.”

One response to “A Million Dollar Humiliation

  1. Written with exquisitely prerequisite humiliation, your short stories never cease to entertain. I wonder what further humiliations await the former red headed ‘Rapunzel’. She may be rich, but money can’t fix sex starved and ugly. Something tells me the stripping of her vanity is far from over.

Leave a Reply