"And you're sure you want Duchess?" Mistress Mertle asked me for a third time, partly confused, partly concerned as I stood there butt naked, fully locked into the ball busting stocks at the bottom of the New York dungeon, Yolo Contendere.
Yolo Contendere is a known entity in the hedge fund industry. Powerful men travel from as far north as Greenwich, Connecticut just to have their balls crushed by the greatest doms this side of the Mississippi.
"Go big or go home!" I responded all nonchalant. Up to this point, I've only ever had my wife squeeze my balls on occasion at home. But she has squeezed hard enough for her hands to hurt and I've always been able to handle it. So how much crazier can this really be I thought. Besides she came recommended by my chief investment officer. I'm way tougher than that pussy.
"Oh hon!" Mistress Mertle, responded while shaking her head. "You have no idea what you're getting yourself into. Our most experienced subs can't handle the Duchess. She's will absolutely fuck up your balls--"
"I'm not a sub," I interrupted her.
Mistress Mertle opened her mouth wide in utter shock while letting out an "Oh ho" laugh. "YOU-DID-NOT-just interrupt me!" She yelled out sternly as if I had offended her god. "I really hope one day you come back here and ask to see me personally. I dare you to ask for me. You'll be choking on your balls before I'm done with you." She paused for effect and then continued. "You won't though," she added in a disinterested tone while looking at her nails. "Ten seconds with the Duchess and you'll be rethinking your life choices."
Just then, another lady dressed in full business casual walked into the room carrying some paperwork. No doubt the waiver I had signed twenty minutes earlier with a different hostess at the entrance.
"What is he doing in here?" She asked Mistress Mertle, clearly annoyed by the situation.
"He asked for the Duchess, by name," Mistress Mertle responded while nodding in my direction.
"He's a NEW CLIENT!" The hostess yelled out.
"Well whada you want from me?" Mistress Mertle responded impatiently.
"I want you to use your head," the hostess fired back while lighty tapping Mertle on the forehead with the paperwork. "How does it help us if he quits after just one session?"
"Well, I already called her," Mertle responded. "She's on her way down now. Look, he already signed the waiver right? And he's a big boy. I tried to warn him but he won't listen. Let him learn the hard way."
The hostess then walked around the stocks and bend down a bit sideways to face me. "Sir, I dont think it's a good idea for you to have a session with Duchess Sybill. She's generally reserved for our, um, most experienced clients. You might be bettet off having an appointment with Mistress Siphi, Lydia or Rae.".
"Look lady. I know all about the Duchess and I want what I want," I said to her. Can we please get on with it now," I added impatiently.
The hostess rolled her eyes, handed Mistress Mertle a small ziplock bag and then stromed off.
Mertle giggled and shook her head as she watched the hostess exit the room. She then opened the bag, pulled out a small object and then came around to the front of the stocks to face me.
"Open your mouth," she said in a semi-serious voice. She was holding a mouth guard.
"What is that?" I asked rhetorically. "I don't need that. I'm fine." I said confidentally.
"Trust me, hon," she quickly responded. "We're here to break your balls. Not your teeth. We know what we're doing. You're going to want this. Now open up.".
Reluctantly, I let her shove the mouth gaurd into my mouth. I also began to wonder whether maybe I had bit off more than I can chew. But the thought was fleeting. "Nah" I said to myself as my cock became rock hard. "I can handle this." I'd never been more turned on in my life.
The light in the room was dimly lit and the walls painted grey and black to resemble a medieval dungeon. The large enclave contained all manner of BDSM toys and devices for the discerning New York elite.
A massive mirror stood fixed a few feet away on the wall directly in front of me. I assume it's to give the clientelle a nice view of the ball beating they were about to receive.
Before I could even finish fully taking in the enviroment, she finally entered the room. The Duchess had arrived. She was all dolled up in spiky high heels, with matching black bra, thigh high lacy hose and a garter covering a red thong. She was strikingly beautiful and she was here to bust my balls.
I couldn't believe it. She was right there in the flesh. The mistress of my greatest fantasy.
She walked toward a black dresser set in the middle of the room and completely ignored my presence. She oepned a drawer that was ominously embroidered in a pinky flowery font that read "Sybill's Balls! and pulled out a few items. The Duchess nodded to mistress Mertle who nodded right back at her. Mertle gave me a wink, cracked a devious smile and then left the room.
The Duchess then began wrapping white boxer's tape around her right knuckles. "Did they mention our rule on the use of a safe word," she asked me while wrapping her knuckles.
"Uh...yes maam," I gargled nervously through the mouth guard.
"Mistress," she corrected me. "Yes. MIS-TRESS." She added a second time while momentarily pausing what she was doing.
"Yes Mistress," I responded in kind.
There was a long pause before she came up behind me, knelt down, wrapped her hand around both of my balls without warning and yanked them way up past my buttchecks.
I jumped and winced a bit on the yank.
She then began to silently tie a hairband aroud the base of my balls.
"Well...personally...I don't like to use safe words," she said while using a few more hairbands to tie off each of my balls separately. "But if you insist. I charge a $1000 penalty every time you use it.".
I sat there silently and didn't respond.
"Understand!?" she said loudly as she squeezed my left testicle harder than my wife had ever squeezed. Searing pain shot though my abdomin as I felt that bone breaking sensation one feels when a testicle is compressed to the limits.
Snot involentarily shot through my nose and my eyes began to water. I was baring down so hard that my teeth were grinding almost right through the rubber mouth guard. I know right then that maybe this was more than I can handle.
I choked out a "yes mistress! Through my grinding teeth."
She then placed each testicle in each of her hands and squeezed even harder this time with her nails digging right into each of my balls. "Thats good! Real good!" She said ignoring my reaction to having my balls crushed in her bare hands.
I knew right then I had never experienced anything like it in my entire life. I was in so much agonizing pain that I couldnt even remember the safe word. I yelled out a STOP once I was able to catch my breath.
"And that's one thousand dollars!" She yelled out. "Dude! We're just getting started! You are not cut out for this you big fucking pussy!"
She then grabbed my balls with her left hand lifted them way up and squeezed them even harder this time. She dug her middle and index finger in my left ball and her pinky and ring finger into my right ball. As each testicle was separately tied off, I honestly thought they were at the precipice of breaking. I felt my heart skip a few beats. This was on several magnitudes worse than what I had just felt a moment earlier. I didnt think it could get any more intense. But boy was I wrong.
Before I could even speak a word, and with her still digging each of her fingers deep into the middle of each testicle, she smashed her right fist squarely into my balls throwing blow after merciless blow. This while maintaining a vice-like squeeze of my separated balls. They were each essentially pinched down in half.
Searing paint shot through my entire body as it felt like each punch was breaking my already deeply compressed testicles. I screamed out high pitched screams with each blow as if I had been burned alive. I couldnt even speak to say the word "stop."
Hit after hit, they kept coming and I was paralyzed unable to speak.
Finally by the 15th punch, I was able to catch a breath to yell out the safe word and she merely yelled back $2,000...$3,000...$4,000 and continued wailing on my balls giving me no time to recouperate.
By the 30th punch, my mouth gaurd had fallen out of my mouth and I beared down as they kept coming one after another. It must have been sometime around the 50th punch that she stopped and began to unwrap the tape around her fists.
Her knuckles were bright red and she started to waive her hand a bit as she winced in pain.
"I think your balls might have sprained my pinky," she said in a nonchalant voice as I sat there groaning in agony unable to talk or even function.