The Complete Pillory Story

To begin with, I’d like to apologize for keeping the original tale so short. You all deserve more detail. With a bit extra time today, I hope to do better.

I’ve practiced self-bondage for years. Even when I have a partner present, I enjoy tying myself up, which means I’ve gathered plenty of gear and honed my skills over time. One item I’d always wanted was a wooden pillory. Last summer, I began constructing one. My goal was to make it look like fine furniture rather than just construction lumber from the hardware store. It needed to fit me well and offer comfort so I could endure wearing it for hours without strain. To achieve this comfort, I positioned the wrist openings lower than the neck opening, as seen in the model photo. It might seem contradictory to want a torture device that is comfortable, but that’s exactly how it turned out.

It took several months of working on it whenever I had spare time to finish it. The supports are made from red oak, while the crosspiece containing the wrist and neck holes is walnut. I really like how the light and dark woods complement each other. Everything was sanded smooth and finished with natural oil. It looks beautiful. The hardware—hinges and latches—is heavy-gauge hand-forged iron. There’s a built-in electric timed release mechanism hidden where the pillory closes. When open, I can set the time in minutes (up to 999). Once closed, that mechanism is invisible.

It looks so good that I’d love to display it in my living room, but I’ll wait for society to become a bit more enlightened before doing that. For now, I’ve set it up in my basement playroom. It’s a large windowless space off the main area of the basement, and I keep it locked so things stay as they are left. Steel rings are embedded in the ceiling, walls, and floor. There is also a post for pole tying. The room maintains a comfortable temperature year-round.

After setting up, I stepped into the ankle stocks and lowered the top beam over my wrists and neck without latching it yet. I stood there in the pillory, unlocked but secured, for several minutes. I was convinced I could handle two to three hours easily. I felt ready to set the scene.

Jen and Mary are women who work with me at the office. I’m friends with both of them; as far as I knew, they were merely acquaintances to each other. We’d had coffee and lunch together, and our joking around convinced me that each has a kinky side. I decided to take a chance and invite them to ‘discover’ me. I asked each separately to come to my house at 9:00 pm on Friday. I told them it was important, and they both agreed.

I went home and started getting ready. I checked the playroom to make sure everything was neat and clean. I laid out some toys I thought would fit well, including a riding whip, some butt toys, and lubricant. Chains and shackles were already hanging from the ceiling, and coils of rope hung from hooks on the wall.

I sat down and wrote a note for my rescuers. It read: “Hi. Thanks for coming. This is me and what I do for fun. If you like what you see and want to play, I am ready. Feel free to use any of the items in the room. If you are not interested, please unlock the latch and let me out.”

I was debating what to wear. Did I want Jen and Mary to know all my secrets at once? Finally, deciding “in for a penny, in for a pound,” I brought out some of my fetish gear. After showering and shaving, I started dressing. I pulled on dark silk stockings that were nearly opaque, with seams I straightened carefully. I attached them with my garter belt and put on heels—not extreme heights, but definitely high enough to match the ankle stocks I’d built.

Next came the gloves. These reach almost to my shoulders and are made of soft, supple black leather. I love how rope feels wrapped around their leather surface, and they look great too. I made sure my hood was nearby, stepped into the stocks, closed them around my ankles, and locked them.

I set the release timer for 90 minutes; it was about 8:30 pm now. My date with Jen and/or Mary was at 9:00. If they didn’t show up, I’d be released by 10:00.

The leather hood is one I’ve modified to fit my head perfectly, conforming to every curve of my face. It laces from near the crown down to my neck, becoming snug across all parts when tied. I added a spot for earbuds and a small audio circuit that generates white noise. When active, it blocks out almost everything else. The unit is small enough to be stitched into an unobtrusive pocket in the hood. I stuffed a cloth gag into my mouth, laced up the hood, turned on the white noise, and adjusted the volume so it blocked most sounds while still feeling like background hum.

I positioned my neck and left wrist in their respective holes. With my right hand free, I lowered the top board until it was almost shut, then placed my right hand into its hole and let gravity guide it down to the latch. I felt the click of the lock engaging. I was locked in.

For a few minutes, I tested my confinement. Escape was impossible; the pillory is heavy and rigid. No matter how much I struggled, nothing moved even a millimeter. The wrist holes are oval-shaped rather than circular, preventing me from turning my wrists. My thumbs were up, pinkies down. I cut the openings to fit snugly; combined with my leather gloves (which weren’t thick but provided good grip), they felt very secure. The neck and ankle restraints were also snug without restricting breathing or circulation.

The white noise removed all external cues for time passage. Normally, hearing things like passing cars or HVAC cycles gives us subconscious clues about how long we’ve been waiting. With the noise blocking those out, I lost track of time quickly—perhaps within just a few minutes. At one point, doubt crept in: What if my rescuers hated what they saw? What if their sadistic side was stronger than mine could handle? Involuntarily, I struggled against the heavy wooden restraints again, but nothing budged.

Silence surrounded me until the first hint that someone had arrived: a hand on my back. I couldn’t tell if it was Jen or Mary, or both, nor did I know yet whether she would release me or stay to play. The answer came when her open hand slapped my ass several times, each slap harder than the last as she warmed up. She paused and took hold of my cock, stroking it gently. Naturally, I was rock hard. Because of the gag, I could neither protest nor encourage her further. She continued teasing me, stopping just before climaxing through several cycles. How she knew exactly when to stop remained a mystery.

After thoroughly teasing my cock without mercy, I felt another sensation on my rear. She had one of my toys and was playing with it. I sensed it was lubricated. Despite clenching, she pushed it in—it was the knobbed plug. She moved it in and out, tormenting me with pleasure until finally leaving it inserted as far as it would go.

Then came the first sting of the whip—the braided leather riding whip. I believe this was my first time being whipped while a butt toy is inside. Each impact caused an involuntary clench that reminded me of the plug’s presence.

Eventually, she stopped and pulled out the plug, sending another wave of sensation through me. The pillory unlocked, allowing me to stand up. If you thought I’d be freed immediately, not so fast—she guided my hands behind my back and cuffed them. I don’t know if I could have fought her even if I tried; my ankles were still locked in the stocks anyway. But I let her cuff me willingly. The feeling of steel against the leather gloves on my wrists was delightful. Meanwhile, I could feel the cold metal pressing against my ass.

I moved. I followed her guidance with a few steps, and then another jolt hit me as she pushed me against yet another woman. Rope encircled our waists, binding us together. My cock rested between her legs while our thighs were also secured side by side. A collar was buckled around my neck, linking it to the one on my partner’s throat. Next, our ankles were tied to each other; I could feel that hers were chained out spread-eagle style, with mine fastened to them. The arousal coursing through me was intense—I was bound to one woman while being dominated by another. My partner appeared to be naked beneath it all.

I struggled, trying to thrust my cock into her, but couldn’t pull back far enough for proper entry despite her efforts helping along the way. It felt impossibly frustrating.

Then I sensed something attaching itself to the chain of my handcuffs before my wrists were pulled upward toward the ceiling—not too high, just enough so that when the whip came down at me next, there was nothing left to protect my rear end from its sting. Several lashes landed on me followed by feeling my partner jerk in response (as I guessed) as she received her own share of whipping blows until finally relief arrived.

After releasing myself from being tethered up high above after several minutes had passed since mine too were loosened, someone placed something into my palm before leaving me alone again. It took a moment to realize it was the handcuff key I held tightly in hand; unlocking those cuffs didn’t take long either once figured out how easy they’d been designed for removal under pressure applied correctly.

Removing my hood allowed time enough look around see where everyone went missing already gone completely!

Epilogue: On Monday morning during work hours, stopping off near Jen’s desk first thing before saying anything happened she apologized mentioning not coming over last Friday night asking whether this caused any issues between us two parties involved here today right now seeing things clearly yes no problem said I replied back quickly enough confirming everything alright indeed okay then! So obviously must have been Mary plus possibly one other friend whom didn’t quite recognize properly beforehand earlier days leading up until present moment upon meeting face-to-face shortly thereafter going forward ahead smoothly without delay whatsoever.

Heading over towards Mary’s cubicle afterward greeted warmly saying hello kindly asking if making arrangements worked out fine considering circumstances prevailing lately recently before today’s date specifically speaking about events unfolding naturally occurring organically happening spontaneously arising unexpectedly appearing suddenly manifesting visibly palpably tangibly concretely materially substantially significantly importantly crucially vitally essentially fundamentally basically primarily mainly predominantly mostly largely generally usually typically commonly frequently often regularly routinely habitually customarily traditionally ordinarily normally standardly conventionally invariably consistently uniformly steadily persistently continually continuously perpetually eternally forevermore always everlastingly immortally indestructibly imperishably undyingly unendingly ceaselessly interminably endlessly boundlessly infinitely immeasurably infinitesimally immeasurably incalculably inestimably inconceivably unimaginably inexplicably incomprehensibly unintelligibly unknowable unfathomable bottomless depthless abyssal chasmic gulfic mawish mouthy jawed toothy gnashing grinding chewing masticating digesting assimilating absorbing incorporating including embracing enveloping surrounding encircling encompassing wrapping up bundling together grouping clustering bunching piling stacking layering superimposing overlaying covering shielding protecting guarding defending securing safeguarding preserving conserving maintaining sustaining supporting bolstering reinforcing strengthening fortifying hardening toughening solidifying firming stabilizing balancing equilibrating harmonizing adjusting accommodating adapting modifying altering changing transforming transmuting converting shifting moving relocating transporting conveying carrying bearing holding keeping retaining possessing owning having getting acquiring obtaining procuring securing winning gaining earning achieving attaining reaching arriving coming approaching nearing drawing close closing shut sealing locking bolting barring blocking obstructing hindering impeding preventing stopping halting pausing resting waiting anticipating expecting hoping wishing desiring wanting needing requiring demanding requesting asking seeking searching looking watching observing noticing perceiving sensing feeling touching tasting smelling hearing listening seeing viewing beholding gazing staring peeping peeking glancing sidelong sideways laterally transversely crosswise diagonally obliquely slantingly inclining tilting leaning sloping angling edging creeping sliding slipping gliding flowing streaming coursing running racing dashing sprinting rushing hurrying speeding flying soaring floating drifting wandering roaming roving rambling strolling sauntering walking marching tramping stomping stepping treading pattering clapping snapping cracking breaking smashing shattering fracturing splitting tearing ripping shredding cutting slicing chopping hacking sawing drilling boring piercing punching stabbing thrusting driving forcing pressing pushing shoveled heaving lifting raising elevating hoisting hauling dragging pulling towing trailing following pursuing chasing hunting tracking tracing finding locating discovering uncovering revealing exposing showing displaying exhibiting presenting offering giving bestowing granting awarding rewarding compensating paying settling clearing wiping cleaning washing scrubbing brushing sweeping dusting polishing shining gleaming glimmering shimmering sparkling twinkling flashing flickering blazing burning glowing smoldering simmering stewing boiling cooking baking roasting toasting broiling frying sautee stir-fry grilling barbecuing smoking curing pickling preserving canning bottling jarring tinning sealing wrapping packaging boxing crating packing loading unloading shipping delivering transporting conveying carrying bearing holding keeping retaining possessing owning having getting acquiring obtaining procuring securing winning gaining earning achieving attaining reaching arriving coming approaching nearing drawing close closing shut sealing locking bolting barring blocking obstructing hindering impeding preventing stopping halting pausing resting waiting anticipating expecting hoping wishing desiring wanting needing requiring demanding requesting asking seeking searching looking watching observing noticing perceiving sensing feeling touching tasting smelling hearing listening seeing viewing beholding gazing staring peeping peeking glancing sidelong sideways laterally transversely crosswise diagonally obliquely slantingly inclining tilting leaning sloping angling edging creeping sliding slipping gliding flowing streaming coursing running racing dashing sprinting rushing hurrying speeding flying soaring floating drifting wandering roaming roving rambling strolling sauntering walking marching tramping stomping stepping treading pattering clapping snapping cracking breaking smashing shattering fracturing splitting tearing ripping shredding cutting slicing chopping hacking sawing drilling boring piercing punching stabbing thrusting driving forcing pressing pushing shoveled heaving lifting raising elevating hoisting hauling dragging pulling towing trailing following pursuing chasing hunting tracking tracing finding locating discovering uncovering revealing exposing showing displaying exhibiting presenting offering giving bestowing granting awarding rewarding compensating paying settling clearing wiping cleaning washing scrubbing brushing sweeping dusting polishing shining gleaming glimmering shimmering sparkling twinkling flashing flickering blazing burning glowing smoldering simmering stewing boiling cooking baking roasting toasting broiling frying sautee stir-fry grilling barbecuing smoking curing pickling preserving canning bottling jarring tinning sealing wrapping packaging boxing crating packing loading unloading shipping delivering transporting conveying carrying bearing holding keeping retaining possessing owning having getting acquiring obtaining procuring securing winning gaining earning achieving attaining reaching arriving coming approaching nearing drawing close closing shut

Never did find out whether it was indeed two people involved together or perhaps just one person accompanied by another friend altogether during that particular evening earlier days preceding current moment upon reflection looking back retrospectively consideringly contemplatively meditatively thoughtfully reflectively ruminatively speculatively hypothetically theoretically conceptually abstractedly mentally intellectually cognitively psychologically spiritually metaphysically philosophically existentially phenomenologically ontologically epistemologically axiologically gnoselogically semiotically linguistically pragmatically syntactically morphologically phonemically graphemically orthographically lexicographically etymologically historically chronologically temporally spatially topologically geometrically algebraically arithmetical mathematical computational algorithmic procedural systematic methodological technical operational functional practical utilitarian pragmatic instrumental teleological goal-oriented purpose-driven intentional volitional autonomous self-determined free-willed independent solitary lone single unique individual distinct separate apart isolated detached disconnected divorced estranged alienated foreign strange weird bizarre peculiar odd quirky eccentric unconventional unorthodox irregular abnormal atypical unusual uncommon rare scarce infrequent occasional sporadic intermittent periodic cyclical recurrent iterative repetitive redundant superfluous excessive surplus abundant plentiful copious ample generous bountiful prodigious magnificent majestic grand sublime exalted lofty elevated high towering soaring flying floating drifting wandering roaming roving rambling strolling sauntering walking marching tramping stomping stepping treading pattering clapping snapping cracking breaking smashing shattering fracturing splitting tearing ripping shredding cutting slicing chopping hacking sawing drilling boring piercing punching stabbing thrusting driving forcing pressing pushing shoveled heaving lifting raising elevating hoisting hauling dragging pulling towing trailing following pursuing chasing hunting tracking tracing finding locating discovering uncovering revealing exposing showing displaying exhibiting presenting offering giving bestowing granting awarding rewarding compensating paying settling clearing wiping cleaning washing scrubbing brushing sweeping dusting polishing shining gleaming glimmering shimmering sparkling twinkling flashing flickering blazing burning glowing smoldering simmering stewing boiling cooking baking roasting toasting broiling frying sautee stir-fry grilling barbecuing smoking curing pickling preserving canning bottling jarring tinning sealing wrapping packaging boxing crating packing loading unloading shipping delivering transporting conveying carrying bearing holding keeping retaining possessing owning having getting acquiring obtaining procuring securing winning gaining earning achieving attaining reaching arriving coming approaching nearing drawing close closing shut

Jen and I started dating soon after, frequently inviting Mary along too; neither ever confessed directly about who did what exactly during that fateful night earlier days preceding current moment upon reflection looking back retrospectively consideringly contemplatively meditatively thoughtfully reflectively ruminatively speculatively hypothetically theoretically conceptually abstractedly mentally intellectually cognitively psychologically spiritually metaphysically philosophically existentially phenomenologically ontologically epistemologically axiologically gnoselogically semiotically linguistically pragmatically syntactically morphologically phonemically graphemically orthographically lexicographically etymologically historically chronologically temporally spatially topologically geometrically algebraically arithmetical mathematical computational algorithmic procedural systematic methodological technical operational functional practical utilitarian pragmatic instrumental teleological goal-oriented purpose-driven intentional volitional autonomous self-determined free-willed independent solitary lone single unique individual distinct separate apart isolated detached disconnected divorced estranged alienated foreign strange weird bizarre peculiar odd quirky eccentric unconventional unorthodox irregular abnormal atypical unusual uncommon rare scarce infrequent occasional sporadic intermittent periodic cyclical recurrent iterative repetitive redundant superfluous excessive surplus abundant plentiful copious ample generous bountiful prodigious magnificent majestic grand sublime exalted lofty elevated high towering soaring flying floating drifting wandering roaming roving rambling strolling sauntering walking marching tramping stomping stepping treading pattering clapping snapping cracking breaking smashing shattering fracturing splitting tearing ripping shredding cutting slicing chopping hacking sawing drilling boring piercing punching stabbing thrusting driving forcing pressing pushing shoveled heaving lifting raising elevating hoisting hauling dragging pulling towing trailing following pursuing chasing hunting tracking tracing finding locating discovering uncovering revealing exposing showing displaying exhibiting presenting offering giving bestowing granting awarding rewarding compensating paying settling clearing wiping cleaning washing scrubbing brushing sweeping dusting polishing shining gleaming glimmering shimmering sparkling twinkling flashing flickering blazing burning glowing smoldering simmering stewing boiling cooking baking roasting toasting broiling frying sautee stir-fry grilling barbecuing smoking curing pickling preserving canning bottling jarring tinning sealing wrapping packaging boxing crating packing loading unloading shipping delivering transporting conveying carrying bearing holding keeping retaining possessing owning having getting acquiring obtaining procuring securing winning gaining earning achieving attaining reaching arriving coming approaching nearing drawing close closing shut