Dominatrix session review – Anniversary orgasm torment

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Chicago and Saint Louis Dominatrix Mistress Simone

Anniversary Orgasm Torment Session

With Chicago Dominatrix, Mistress Simone
chicago mistress simone

Chicago Mistress

3/28/26

I had specifically requested this particular date for our monthly session because it was the six-year anniversary  (Anniversary celebrations with my submissives are very important to Mistress. It marks important mile stone in our power exchange). of our first phone call. After gifting Ma’am with a few presents (I enjoy receiving gifts from my slaves and submissives. Noting important dates are key in power exchanges) , She clipped our usual “introductory” period short and I was very soon after naked and headed for the table. Notably, my chastity device – usually removed at the beginning of our playtime so that Ma’am can have access to tease and torment – remained locked in place. (Mistress note – You are released from chastity on my authority , not your desires.) As exciting as this change in routine was, it was also slightly alarming, as She had not granted me an orgasm during our previous session, which meant I was now two months without relief.

   Very quickly She had me laid out flat on my back, legs cuffed and spread open and my hands ensconced in thick leather bondage gloves. My arms were chained to the sides of the table in an awkward sort of “begging puppy” position. She blindfolded me before adding the piece de resistance – sliding a dildo into my mouth. I was ordered to keep it from falling, whilst simultaneously strictly warned against using my teeth. As my hands were unable to reach far enough to hold it in place, She clipped a bar to the mitts, which with some maneuvering, I could set atop the dildo’s base. However, at the same time, She also added clamps to my nipples and connected them up to the whole rapidly expanding latticework above me. I was then alternately ordered to either “Suck!” or “Stop sucking!” as She went about wiring my testicles and an anal plug to Her electrical boxes. Still, it was not quite enough to satisfy Her taste for predicament that day, so She began to rotate either jamming the vibrating want against my cage, shoving ice packs into my groin, or just smacking me with… something. (I’m usually blindfolded or facing away and rarely have any idea until we are done and tidying up the full range of implements that have been used against me that day.) Every so often, after a few agonizing strikes to my nipples, She would seize the end of the dildo and personally set a far more energetic pace for its pistoning in and out of my mouth.

At some point, Ma’am decided to put the question of my potential orgasm up for a vote from Her online followers. I was reduced to little more than a scrap of content for the passing amusement of Her audience. It was definitely a unique modern twist on dehumanization and more than a little worrisome as the numbers began coming in.

Before that, however, Ma’am decreed it was time for my “Anniversary spankings” – ten for each year we had been together. My current bonds were undone, and I was shuffled off to the other table to be secured so as to present my backside for punishment. Oh, and the dildo made the trip with us and once my hands and legs were locked down, I was yet again ordered into a cycle of sucking and stopping. When it comes to “special occasion beatings” Ma’am is not one to pull Her punches, and so, after demanding that I “suck more” and “count less” I eventually received all 60 strokes commemorating our special journey of power exchange together.

Time was drawing nigh for the finale of the afternoon, and we switched tables again. This time I donned my new leather hood – its grand debut – custom ordered to fit a bit more properly. It was certainly tighter, but Ma’am likes it tight on Her playthings. I crawled into my leather sleepsack and another electric anal plug was inserted inside me. In addition, clamps were added to my nipples before zipping me up. As I mentioned, the new hood was very tight and being so thoroughly encased and bound in leather was a very heady experience. Ma’am kept busy, occasionally checking in on the vote. At one point She sat on my chest and while I always relish any occasion where I am in contact with Her divine bottom (It’s one of my big fetishes) She sat directly on one of my clamped nipples. To Her credit, She only squirmed once or twice before lifting Her weight off.

I don’t quite remember, it may have been after this moment, but at some point I distinctly recall Ma’am asking if I was miserable yet. And I responded no. Because, while pain, fear, horniness, frustration, humiliation even degradation are all things She has made me feel in the six years I have been seeing Her, She had never made me truly miserable. No matter what hell She puts me through, the few hours I get to spend in Her presence are always the highlight of my entire month. Until the next time.

Oh, and the vote? I lost. 61% to 32%.