Maritta was kind enough to give feedback concerning several typos in my recent posts. As thanks, I gave her a new visit to the Resort and her first diabolically gruesome encounter with the Crimson Executioner...

I’d heard rumors concerning the Crimson Executioner, a former Resort vacation club member for over thirty years until a few years ago when he joined the Resort’s dungeon staff. They say that he’s an evil, sadistic fiend, well known for his barbaric cruelty. Any woman lucky enough to fall into his clutches is fated to suffer a gruesome, agonizing death with no hope of mercy.

A Resort concierge service member escorted me to the Crimson Executioner’s private torture chamber high within the Resort’s North Tower. He was waiting inside the door, dressed in his distinctive red executioner’s uniform.

“Good evening, Maritta. I’ve eagerly awaited your first perilous visit to my private torture chamber. I promise our encounter will haunt your darkest nightmares for years to come.”

Taking my hand, he led me to a post-mounted St. Andrew’s cross, positioning me face-first against the X-shaped wooden restraint as he secured my wrists and ankles. Then, forcing a large ballgag deep into my mouth, he grabbed the back of my revealing bodysuit and brutally ripped it from my body.

I was naked, except for my crimson-red high heels, and yet, what happened next came as a complete surprise. I’d expected whips, perhaps red-hot irons or skewers, into my ass or through my kidneys. Instead, the Crimson Executioner used me sexually, burying his massive erection, cervix deep, in a single powerful thrust.

He used me ruthlessly for what felt like hours, each powerful thrust of his cock driving me helplessly toward my next overpowering orgasm. I can’t remember how many times I came, and honestly, I stopped counting after my twentieth orgasm.

When he finally reached orgasm and climaxed deep inside me, a faint whimper of erotic disappointment escaped around that ballgag filling my mouth as I felt his still erect cock slipping out of me. A moment later, I screamed in agony, my sexual disappointment turning instantly into agonizing pain as he mercilessly drove his cock, balls deep, into my ass.

With nothing for lubricant other than the lingering traces of my arousal coating the massive shaft of his rock-hard cock, it felt like he was ripping my insides apart with each powerful thrust. While no stranger to the painful pleasures of anal sex, this far exceeded even my darkest masochistic cravings. The bulging head of his cock wasn’t buried deep within my rectum. Instead, it penetrated brutally deep into my colon with each powerful thrust. At first, the pain was overwhelming, but sadistically, he continued ravaging me. Then, the agonizing torment I was helplessly enduring shifted slowly to pleasure as I experienced my first anal orgasm of the night. And, yes, I quickly lost count of those as well. His cruel anal assault lasted far longer than my masochistic mind could derive pleasure from the unrelenting agony I was experiencing before, with one final agonizing thrust, he climaxed deep inside my intestines.

Completely exhausted, I offered no resistance when he unlocked the restraints from around my wrists and, pulling my arms behind my back, used a leather strap to buckle my wrists tightly together. A second strap went around my elbows, pulling them painfully back until they touched. Then, releasing my ankles, the Crimson Executioner roughly pulled me to my feet.

Removing the ballgag from my mouth, the Crimson Executioner dragged me helplessly toward the Iron Maiden, “Well, Maritta. Now that we’ve dispensed with the pleasurable part of our evening, it’s time to surrender yourself to the pain.”

Within moments, I found myself tightly restrained within the Iron Maiden’s claustrophobic metal sarcophagus, staring in horror at the rows of razor-sharp spikes lining the interior of its slowly closing door.

“Maritta. Dying within the Iron Maiden is never an easy or quick death. You will helplessly endure several days of screaming in unrelenting, inescapable, agonizing torment before you finally finish bleeding to death for my amusement.”

Death in the Iron Maiden has haunted my darkest erotic nightmares since I first noticed one within one of the North Tower’s torture chambers shortly after I joined the Resort’s vacation club. Still, I felt an overwhelming sensation of terror at the Crimson Executioner’s words. Even accepting the reality that I’m a submissively masochistic pain slut with an unquenchable death wish, deep down, I wasn’t entirely sure I was ready to die like this. And yet, I had no choice. Here, in the torture chambers of the Resort’s North Tower, the only expectation of mercy is death.

Staring into the Crimson Executioner’s cold, cruel eyes, even with his face concealing leather hood, I could see the look of eager, sadistic anticipation as he slowly closed the Iron Maiden’s horrifying spike-lined door. I instinctively knew he was slowly closing that door on purpose, gleefully using every lingering second to heighten my already overwhelming terror before those spikes painfully reached my flesh.

Still, I managed to avoid screaming until those two horrifying spikes reached my eyes. An instant before the Iron Maiden’s other diabolically positioned spikes pierced my body as its door finally locked closed.

The Crimson Executioner was right. Slowly dying within the Iron Maiden’s horrifying spike-lined sarcophagus was one of the most profoundly disturbing and ghastly obscene deaths I’ve ever endured here at the Resort.

Late the next day, after I awoke from regeneration, the technician told me I’d endured 54 hours of unrelenting, agonizing torment within that Iron Maiden before I finished bleeding to death. A faint grin of amusement appeared on the technician’s face at the sudden look of horror that appeared in my eyes as she added, “54 hours, not bad, but hardly a record. To break that record, you would need to last at least 73 hours before you died.

Several nights later, safely back within her Resort villa, Maritta watched the storm coming ashore across the rocky beach below.

Turns out the Crimson Executioner had been right. Her unspeakably brutal experience within that horrifying Iron Maiden still haunted her nightmares whenever she closed her eyes. Still, perhaps she should request another session with the Crimson Executioner. After all, the Iron Maiden’s record was only 73 hours...