A Long Journey of Play into Night – Part 1

A Long Journey of Play into Night - Part 1

Part 1: A Long Journey of Play into Night

From munches, clubs, events, expended adventures with my wife, and continued sessions with a pro-Domme, I fully expected the trajectory of my fet-exploration to have led to some play dates by now.

Alas, it has proven to be most difficult for a male sub in Chicago, where it seems that most Mistresses are either professionals, have single slaves serving them, or have adoring hordes of potential bottoms anxious to subjugate themselves. Get in line.

My losing streak seemed like it might be ending a couple of weeks ago when I had arranged for a meet-up during a business trip to London. While no promises of play were offered, after numerous communications and specific arrangements, the chance to connect certainly seemed strong. The meeting, however, never took place. My ‘date’ had to cancel due to a medical emergency (another story!).

My strategy changed for my business trip to NYC this past weekend. After some cursory explorations into events and possible meet-ups, I came to conclusion that even though the ratio of female Dommes to male subs in NYC seemed MUCH more favorable than in Chicago, my best and most efficient way to gain some new D/s experiences would require going the pro route. My amazing and understanding wife/Mistress gave me permission to explore, and soon I had multiple potential scenarios in place. By Saturday plans were in place for a 6pm Sunday rendezvous with the gorgeous Mistress Madison at the renowned NYC dungeon Pandora’s Box.

Sunday morning dragged by – checking my iPhone incessantly in anticipation of the final confirmation and directions to the facility. When the email hadn’t arrived by 4pm I called in – and was shocked to learn that the appointment had been cancelled because I failed to confirm (a bit of information that was never shared)! Moreover, Mistress Madison could not be reached, and Isabelle, who had taken the reservation, was the only one who had her contact info.

Shit. It was looking now as though I couldn’t even buy play.

Fortunately after a number of phone calls Madison was located, and the date was back on – though potentially delayed. I showed up at 6:00pm anyway, bringing a small gift of Lindt chocolate truffles for both Madison and Isabelle: milk chocolate for Isabelle, and the dark chocolate “blue balls” especially for my Mistress. 😉

Madison had yet to arrive, but Isabelle was there and graciously welcomed me – coming as close to apologetic as a Domme is likely to get with a sub for the scheduling mix-up. We soon dove deep into conversation, which was soon accommodated by a bottle of wine. Isabelle was amazing. She had worked at Pandora’s Box since 1995 (with a short respite in France), and while still doing sessions, seemed to be primarily now assuming the role of den mother and office manager. We maintained a fluid conversation despite her fielding a steady steam of phone calls, buzzing in visitors and attending to unseen offstage demands.

“I’m sure,” I said, “you’ve got your share of wild stories.” She acknowledged this truth with a knowing laugh. “Yours might be another one of them,” she slyly quipped.

By 6:30pm Madison had arrived and was prepping for the session. About 15 minutes later Isabelle checked on her progress. Not ready yet. Isabelle mentioned, humorously, how difficult it was trying to manage Dommes. I didn’t really care about the delay. I wasn’t in any rush, and was most enjoying the wine and Isabelle’s company. My session finally begin about an hour after the original scheduled time, at which point I was quite relaxed and ready to for adventure.

During a brief pre-session consultation in a small waiting room Mistress Madison was all business. Statuesque and stunning – a dead ringer for Scarlett Johansson – she quickly drilled me in an unmistakable NYC accent that had no doubt been diminished, but would likely always be part of her charm. “First time?” she asked. “You or me?’ I joked – assuming that this pre-scene chat would be out of character. She allowed only a split-second to appreciate the humor before fully regaining command.

A short time after our first brief conference, Mistress strode into the dungeon room where I waited, absolutely striking in her red latex top and black skirt. I soaked in her jaw-dropping, knee-buckling splendor, sinking in the far end of the pleather couch. Madison admonished me for sitting there and ordered me off the couch and to strip. “Down on your hands and knees,” she ordered. “Forehead on the ground.” I assumed the position, and she continued: “This is how you should greet your Mistress” she offered – part lesson, part scolding.

While I indicated that I wasn’t into pain, Mistress informed me that some spanking was requisite because she enjoyed it so much – though my low pain-threshold would absolutely be respected. “For each spank,” Madison instructed, “you must count the number and reply: ‘Thank you, Mistress.’” Despite a minor reprimand for counting prematurely on one whack, I made it through this task without error.

“Next, you’ll count backwards from 10 with each spank.” Foolishly (nerves? purposeful insolence? a bit too much wine?), I made another attempt at levity. “Mistress,” I began – displaying some measure of decorum – “this feels like a field sobriety test.” Madison was clearly not amused – but picked on the quip without missing a beat, demanding that I now “get up!” walk a straight line and touch my nose. I was a bit shaky – not sure if I would passed!

“Now turn around,” she demanded. Fully exposed, she looked me over – insulting my “pathetic excuse for a cock” which was fully erect and at attention for the inspection. Displaying some adept rope skills Mistress quickly bound my cock with a clever criss-cross knot, leaving a significant length for a lead, which she now tugged on tauntingly. She had my undivided attention now – there would be no vain attempts at humor from here on out.

The setting of the “The China Doll Room” (aka the “Pretty in Pink Salon”) should have prepared me for what came next. Mistress revealed a black thong with tiny hearts, which she taunted me with before demanding that I use it to cover-up my “useless clit-cock.”

“That’s a good sissy slut,” she encouraged, as I awkwardly donned the tiny panties. Once they were in place Madison yanked on them forcefully, the cheek floss wedging tightly up into my ass as her haughty laugh reflected a mixture of amusement and distain. “I want you to tell me how your pussy is dripping wet,” ordered Madison, “and aching to be fucked.” Though my voice was cracked and hushed in humility, I didn’t hesitate.

The next step of my sissification was a pair of chunky, 3-inch high ankle strap wedges, which I slipped into less than gracefully, but with little delay. Mistress commanded me to parade around in my heels and panties, to look at myself in the mirror and to again tell her about my hot, wet cunt. I was flush with shame – experiencing that amazing contradictory blend of mortification and sexual arousal.

Next, Madison instructed me to untie some knotted ropes, laying the unleashed cords across the top of a three-foot high whipping horse. She then led me by my cock-leash, bending me over the whipping horse and tying my ankles in place. Bound to the elevated wood bench with my legs fully spread apart left me fully vulnerable to Mistress’ whim. She spanked and paddled me while continuing her assault of verbal humiliation.

Having sufficiently pleased Mistress I was now granted the honor of shining her latex skirt. While the session up to now was stimulating, ultimately it’s some nearly impossible balance between compassion and cruelty, degradation and kindness that gets me most turned on. These seemingly contradictory emotions deliver a sensuality and intimacy that I crave, and now I was feeling the full push and pull of these sensations. The touch of latex, the proximity of Madison’s ass and pussy, and soothing feel of rubbing of gel over her smooth black skirt, the cigarette smoke billowing from her lips. I soaked it in. Madison towered over me like a goddess, supervising my polishing work. Without missing a beat I willingly received a cigarette ash that she flicked into my mouth, before redirecting my attention back to the primary task.

Mistress now ordered me onto my back, her mystifying latex clad body straddling me. She suggested I might want to close my eyes, but there was no way I was going to divert my glaze from the wondrous, unattainable chasm that hovered above my face. Mistress’ bountiful stream of golden pee was the wonderfully degrading coup de grace. “Don’t miss a drop,” she tormented, “and I may allow you to cum.” I didn’t, and see did.

Overall the session with Madison was exciting, fun and certainly expanded tremendously the parameters of my previous explorations. It also helped me to better understand a couple of things regarding my kinkiness: 1) my desire for heightened intimacy and caring along with a healthy does of degradation and abuse, and 2) ultimately I’m not fully pleased if Mistress isn’t thoroughly enjoying the session as well (i.e., aroused). So while a drop-dead gorgeous and ceaselessly cruel Mistress such as Madison is any subs dream, my ideal session would preferably have another dimension. Are my expectations too high? No doubt. But I’ve been spoiled, I suppose, by my two Mistresses who are so aligned with my kinkiness! I suspect that the response from traditional fetdom might be one or more of the following: 1) as a sub you have no right to want, yet alone expect, anything, 2) you need to earn that right for any of your Mistress’ compassion, and 3) it’s really not up to you, now is it? Guess, along with a host of other contradictions, I’m a bit of a demanding sub!

I had requested a post-session consultation and Madison obliged. We both sat with Isabelle and continued to drink wine and chat. While Isabelle maintained a clearly dominate demeanor, she wasn’t afraid to let her nurturing side show. Not so Mistress Madison. Perhaps caustic and demanding was her 24/7 personality. Perhaps she was just continuing to role-play and the scene clearly wasn’t over yet!

There was a steady stream of activity. Phone calls, vistors, Dommes. When a caller was buzzed in, I was sent like a guilty schoolboy into the corner of the entry area to maintain necessary discretion. But although I was had been loitering for some time now, there was no hint that I had overstayed my welcome. I was in no rush, so thrilled to linger on!

Indeed, my night of play in the dungeon was just beginning… (to be continued!)