Bondage Sessions: Your Punishment

As I reflect back on many years of sessions with professional dominatrices, trying to scratch a specific itch that could never quite be reached, I realize I've experienced some wild and incredible things. From profound pleasure to extraordinary danger, and everything in between, I've seen a lot. I'm starting a process of writing these experiences into stories so that others could learn from my mistakes, and maybe even experience some vicarious enjoyment. These stories are based on real experiences, but names, locations, and some details have been changed so that no individuals can be identified. I have not chapterized these stories as they are not necessarily intended to be serial.

I'll also include the disclaimer that all participants described in this story were over 18 when these events took place.

After several years of on-and-off sessions with many different pro dommes, I found myself craving new experiences and gravitating toward online ads that were unusual. There were a number of pros who advertised frequently, many of whom I had seen one or more times, and I got to a point where I was skipping right over those and only stopping when something new and different popped up.

My interests had not changed; I still wanted to experience bondage, restraint, and captivity at the hands of a skilled professional. But I found sessions with the regular pro dommes in the local community were becoming tedious and formulaic, and I longed for something "different."

Ad ad appeared on one of the adult classified sites one day that I had not seen before. The subject line was "Find your punishment here..." and the ad went on to describe some fairly sadistic services including being beaten, flogged, whipped, marked, etc. There was even a disclaimer that those looking for "soft" services should look elsewhere. The photos included in the ad looked authentic and not professionally airbrushed and photoshopped (cheesy studio-sanitized ad photos are another telltale sign of a dull session). The photos depicted a young, attractive goth-looking woman bearing some thick chains and other instruments of pain and torture.

It might have just been the horny man in me responding to the erotic imagery of a young attractive woman with so much BDSM gear, but something inexplicable drew me to the ad. The services described couldn't have been further from my interests, but the "what if...?" in the back of my mind tempted me to respond. I asked if she would consider a session that was focused on heavy bondage and restraint, without any of the sadistic elements.

Surprisingly, I received a reply quickly reading, "That is within my skill set," and outlining a reasonable cost, and the condition that we must meet in a public place first. We corresponded briefly and agreed upon a meeting place in a coffee shop. She told me to call her "Robin."

I met Robin two days later in the agreed-upon coffee shop. I was immediately uneasy by our appearance together; me, the middle-aged guy in work clothes, already out of place in this hipster environment. Her, in a slinky black dress, easily 15 years younger than me. After I bought us both coffee, we sat across from each other somewhat awkwardly and made small talk. She was quite thin and diminutive with tangled black hair and sultry eyes. She did not look comfortable in the little black dress she wore, as if maybe cargo pants and a black t-shirt were more her style. We did not talk about our potential activities, and after a few minutes she said she was ready to go, and hoped we could meet again.

We corresponded again over email and agreed to schedule a session. She mentioned that she preferred to stay "in character" from start to finish in the session, so all details needed to be worked out ahead of time. Even the payment needed to be handled in a specific way that stayed in the spirit of the session. I had not done a session this way before; in my past experiences there were always a few moments of negotiation and open talk before a session began. She gave me a few more details, including a safeword which would immediately bring our session to an end, and instructions to bring a change of clothes, and wear something that could get dirty. I found that last part tantalizing, hinting at an outdoor setting of some kind.

I met Robin on a cool spring afternoon at the designated place, which was a street intersection downtown. I waited, my anxiety at the unknown of what was about to happen building for only a moment before seeing her crossing the street toward me. She was all business, scowling at me from a distance, walking swiftly and purposefully toward me. She was clothed in a more masculine and utilitarian way than our previous encounter, with baggy black pants and a nondescript t-shirt, her hair tucked into a round black hat. Covering the bottoms of her pants, she wore black Doc Marten style boots. Despite her boyish outfit, she had petite feminine curves, and was attractive, if not stunning, in a natural kind of way.

When Robin reached me, she held out a pair of pink sunglasses, saying nothing, but clearly indicating I should put them on. Carrying only a small backpack that had my change of clothes, I took the sunglasses, raising them to my eyes, only to realize they were covered on the inside with electrical tape, effectively blinding me. Once I put them on, she took me by the hand and we began to walk. It was truly terrifying walking down the city sidewalk completely blind. This was balanced by the novelty of walking hand-in-hand down a public street with a beautiful young woman. I found I could see just a bit of the sidewalk at my feet under the rims of the sunglasses, and I used this to the best of my ability to avoid tripping or walking into anything. We walked two blocks, maybe three, ending up in a residential area.

Robin eventually turned sharply and guided us into a driveway, then through a wooden gate into what seemed to be the backyard of a house. Once inside the gate, she immediately said "down" sharply, and I fell to my knees. I felt her pull my the backpack off my shoulder. The ground was still wet and muddy from the previous day's rain, and the knees of my pants felt cold and wet right away.

Robin came around behind me, pulling my hands behind my back and roughly wrapping my wrists with a short length of rope. When she finished, she stepped way for a moment and I wriggled my bound wrists briefly, finding that the rope was tight, but not expertly applied, and I could probably wriggle out in moments if I wanted to.

As I contemplated this with slight disappointment, I heard Robin walk back toward me, continuing to step with heavy, purposeful strides which I believed were meant to be intimidating. Still wearing the pink sunglasses, I could only see the ground right in front of me. I heard the crinkling of plastic and then felt a plastic bag go over my head, down to neck level. Panic rose in me quickly. How fast will I suffocate with my face covered in plastic? Is this a huge mistake? Robin paused for a moment, as if to give me just enough time to freak out a bit, then I felt her finger pushing through the plastic into my mouth. It kept pushing until it had formed a hole in the plastic which was large enough for me to breathe through. This probably went against 10 different BDSM safety rules, but I didn't feel in imminent danger.

Robin withdrew for a minute again, and I could hear her gathering some supplies. I remained on my knees, blinded by the ridiculous sunglasses, my pants getting wetter and wetter from the saturated ground. When robin came back, I heard the sound of water sloshing around, and I felt something plop against the plastic bag covering my head. I couldn't tell what it was, but I could tell it was wet even through the plastic bag. It felt like maybe a wet rag or paper towel. Another went on, then another. More still, until my entire head was covered in wet cloth. Something was holding all of them together, as they didn't slip off the plastic bag once they were applied. She stepped away once she was finished, and I was left contemplating what on earth was covering my head and face.

After a few moments, I realized the covering was growing hard and it finally dawned on me what it was. Plaster, like the kind that is used to make casts. It was drying against me, in the shape of my head and face. It was a truly strange sensation to feel the plaster solidifying against my face, hardening significantly now as I poked at it with my tongue through my cheek.

Robin came back, and hauled me up to a standing position by the arm. Now that the plaster covered my face in addition to the sunglasses, I couldn't see anything at all. She led me a few steps away into what felt like a structure, but not a house. A shed maybe? She pushed my body around, positioning me precisely for some unseen purpose. I found myself kneeling again, this time hunched down, my hands on the ground in front of me, back bent to keep my head low.

The next thing I heard was a drilling sound, and I felt a piece of wood in contact with the top of my head. As the drilling continued, it felt like the wood was being held more firmly in place atop my head, and likely out in front of me. I felt more pieces of wood come together in contact with my body, and they were quickly attached to each other with screws. Slowly but surely, a wooden box was being constructed around me. A cage, I realized. I was impressed and slightly terrified at how quickly and efficiently the few pieces of wood had become a solid box, with all sides pushing against some part of my kneeling, bent-over body. I am not a claustrophobic person, but the realization of how sturdy this structure was becoming and the relatively uncomfortable positioning of my body were combining to cause me some serious concern. My hands were still tied behind my back, and though her rope work had never felt like it could withstand more than a few twists of my hands, the futility of even trying to free my hands was evident.

The sounds of wood against wood and screwdriver screeching suddenly came to a halt, and all was quiet. I was as surely as captive as I had ever been in any bondage experience. At this, I realized I was fully hard inside my pants, with absolutely nothing to do about it. I had felt some arousal in previous moments as Robin had tied my hands and moved me around, but this was the first time I had been aware of being fully erect.

Though I could hear Robin stomping around and banging materials, she left me alone for several minutes. During this time I could only sit and listen as I tried to imagine what she was doing. Perhaps just going about her normal routine as her captive prisoner sat helpless inside a wooden box, in her shed. I realized how powerless I was, how awful it would be if I were left here for any significant length of time. This drove me to further arousal as I contemplated my shameful perversion. Who in their right mind likes this shit?

Eventually, as my joints began to ache from my bent-over kneeling position, I heard Robin approach and suddenly the drill was running again, either adding more structure to my cage, or taking it apart. It quickly became clear it was the latter, as pieces of wood started to come away, ultimately allowing me to sit fully up in my kneeling position, relieving my aching back. Once most of the structure was gone, I heard Robin take a hammer to the remaining pieces, and they fell away with slightly terrifying blows from the hammer.

Robin then grabbed my arm again and hauled me to a standing position. She led me just a few steps within the shed, and I felt a surface contact my midsection. "Lay on the table," Robin directed. Her words, after so much interaction with no communication, felt heavy and consuming. Still blind from the plaster covering my head, but assuming the surface I felt was the table she had mentioned, I leaned forward against it, ultimately falling forward on to the surface face-down, still partially standing. "On the table!" She repeated, sharper this time. I had no idea how big this table was or how I could get myself on to it with my hands still tied behind my back, but I tried to pull one leg up and crawl forward. I felt Robin's hands roughly pushing my legs, aiding in the effort. After much awkward wriggling and sliding, my legs were partially on the table. Though they were still hanging off the end of the table, Robin seemed satisfied, and stopped pushing.

I felt something go across my back, a rope or cord of some kind, and I heard Robin connecting it under the table, and I felt it pull tight across my back. Then another, and another until there was several of these cords across my back, connected somewhere under the table. I realized after a bit of wriggling that they were stretchy, and decided they were bungee cords. With me laying face down on the table and several of these pulled tightly across my back, I was mostly secured to the table.

But Robin didn't stop there. I felt more bungee cords going around my ankles and legs, and finally one connecting my ankles to my wrists, pulling them together. I was hogtied. I felt Robin mount the table beside me and attach one more bungee around my bound wrists, and under my abdomen, holding my wrists tight against my back. While working the bungee cord under me before pulling it around to connect behind me, Robin's hand grazed my hard cock through my pants. After so much of our time together had passed with almost no contact at all, this brief contact, clearly a careless mistake on her part, sent a shock through my body. Though this was as much sexual contact as I would experience this day, it was a thrill I'll never forget. Sometimes the most intense sexual contact can be an accidental or forsaken touch like this, as powerful as the best blowjob, and far less fleeting.

Robin left me tied to the table like this for quite a while, again banging around within earshot but completely ignoring me. I was totally stuck, covered from neck to knees with bungee cords wrapped around the table, and I resigned myself to waiting for Robin's next move.

After some time, her next move came in the form of the cold metal of some kind of cutting tool against the back of my head. She began to slowly cut a straight line in the plaster from the base of my neck up to the middle of my head. After that, she was able to stretch it a bit, and pull it completely off of me, removing the plastic bag and sunglasses as well. I could see, for the first time in quite a while, though there wasn't much to see inside the dark shed. I saw the pieces of wood that had been my makeshift cage laying in a pile, and the dark wet dirt floor of the shed which had thoroughly soiled the knees of my pants.

Robin began the painstaking process of releasing the bungee cords that held me to the table. Once that was done, she quickly untied my hands, and pulled me roughly off the table and to my feet. She reached behind her, producing my backpack and placing it on the table. "Get dressed," she commanded, before turning and exiting the shed, closing the door behind her and forcing me to disrobe and pull on my clean clothes in the near pitch black of the shed.

When Robin reentered the shed, I had just finished putting my clean clothes on. As we had agreed upon in our emails leading up to the session, she held out her hand saying only, "Tribute." I placed the cash I had stashed in my pocket in her hand. She quickly pocketed the money, then produced the pink sunglasses again, putting them over my eyes. She led me out of the shed, then back through the gate we had entered the yard through. Once out on the sidewalk, she led me roughly a block down the street before grabbing the sunglasses from my face, turning the other direction, and walking away without a word.

As I walked back to my parked car, I reflected on the surreal experience. Though I was disappointed there had not been any sexual release and only the briefest of any contact that could be considered erotic, I was satisfied overall. This had been the most authentic feeling session I had yet experienced, bordering on "too real" more than once. I longed for more, and contemplated whether she would cut off contact with me if I asked for sexual release.

A week later we did another similar session, this one in a different location. I had decided not to ask directly about sexual release or contact, hoping it might evolve organically. After the same process of meeting on a street corner and donning the blinding sunglasses, Robin led me to what seemed like a ragtag apartment building. She took me up several floors in a fright elevator to a messy apartment with loud experimental music playing, and tied me down to a wooden palate, face up. She left me like that for some time, banging around nearby as she had in our previous session. I figured she must have noticed my hard cock pushing up visibly in my pants, but if she did notice, she hadn't reacted to it. She eventually untied me and led me into what seemed to be a shared bathroom. She took me into a toilet stall occupied by what appeared to be a non-functional toilet, and proceeded to tie me up inside the stall, attaching several ropes to the broken toilet and the stall walls. It was unconventional bondage to be sure, but it held me in place quite effectively. I was rock hard the whole time, and she brushed against the bulge in my pants more than once, but paid no overt attention to my cock or my reaction to being inadvertently touched. After securing me in the stall, she closed the stall door and took all of her clothes off. I couldn't see her actually disrobing, but I could see just far enough under the stall door when her clothes landed on the floor in a heap. She proceeded to take a long, steamy shower, which I could only hear, but seemed quite close to me. She whistled most of the time, as if this were just a normal routine for her.

That session ended much as the first one had, with her marching me blind down the street a few blocks before disappearing. I waited a few days after that session, and then worked up the courage to contact her again and ask if we could incorporate sexual release into our next session.

Robin replied swiftly, as she usually did, to my great relief indicating that this was acceptable, though it would cost more. She wanted to pre-arrange many of the details so that she could still remain "in character" for the whole session.

I arrived for our session at the designated corner, and Robin took us once again to the apartment building we had been in previously. I noted that she was dressed differently than in our first sessions. Instead of the utilitarian pants and t-shirt, she wore a long skirt and tank top that showed just a provocative hint of slim midriff.

She had placed a large cargo cart near the freight elevator, and when we arrived in the building, she pushed me into the cart and quickly tied me up with a small rope and some bungee cords. She then rolled me in the cart into the freight elevator, up several floors, and into what was presumably the same apartment we had been in previously.

Upon arriving at the apartment, Robin tipped the cart over, toppling me out onto the hardwood floor. She hauled me up to a standing position, pushing me into a wooden chair that was placed in the middle of the room. She quickly but securely tied me into the chair, with my hands behind the chair back, and my feet tied to the chair legs. Everything that had happened so far was entirely consistent with our previous sessions, but it was at that moment everything changed. She ran her hands over my body quickly, finding my hard cock through my pants, and began the process of unbuttoning and unzipping my pants. She stood over me, leaning forward so that her bra-less chest grazed my face, her small, perky breasts bumping my nose. She pushed and pulled until she had my cock free, and then, coating her hands with olive oil, proceeded to start a firm and quite skillful handjob.