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.
After a year or two of visits to professional dominatrices, I reached a point where the initial thrill of having my deepest fantasies come to life diminished. Though I had a few favorites, the majority of the sessions I arranged felt formulaic, contrived, and disappointing. More than once, I would schedule a 60 minute session, agreeing on rope bondage and domination, and end up in a hotel room with an escort / dominatrix who would put some toy handcuffs on me, jack me off, and send me on my way in 15 minutes.
These experiences caused me to long for more authentic, organic sessions. I looked for dommes who appeared to participate in BDSM as a lifestyle, and not just a job. This led me to some of the more niche web BDSM-focused sites that straddled the line between classifieds and personals. On one such site, I found the profile of a woman named Christine, whose profile description indicated she was looking for paid sessions but open to a long term arrangement. I contacted her through the site, and we corresponded a bit, concluding that our interests in bondage and domination aligned well. She was vague about what specifically she was looking for, but seemed enthusiastic about my interest in being tied up, teased, and dominated.
When our correspondence progressed to the point of planning a meeting, she asked that we meet first in a public place, so we could talk in-person, in a safe setting for her. This seemed like a completely reasonable idea, though it wasn't something I had experienced before.
We met at a busy coffee shop. From her profile photos, I didn't have a clear idea of what Christine looked like, so I was eager to find out if she was attractive or not. I had given her an exact description of what I was wearing, so she found me first, and sat down across from me at a small table. I briefly took her in. She had an average build, not supermodel stunning by any stretch, but also not unattractive. She had green eyes, a completely unremarkable face, and was of medium height. She was wearing baggy jeans, a polo shirt, and a purple baseball cap with a brown ponytail sticking out the back. The combination of polo shirt and baseball cap gave her a tomboy affect, though the shirt was loose around her neck and unbuttoned to the point where I thought I could see a tiny bit of the top of her bra.
We greeted each other and spoke briefly. I was nervous and awkward, and she seemed to match my nervousness, which surprised me a bit. After a few rounds of small talk, we agreed that we should set up a "private meeting." It felt strange to begin talking about this openly in such a public place, but the coffee shop was buzzing and no one was paying any attention to us.
"I do all of my sessions on my boat," she said, "it's not far from here." That was a surprise, albeit a pleasant one. I had never even contemplated doing a bondage session on a boat. It added more mystique to her already mysterious persona.
"Great," I replied, trying not to show my surprise, "do you mean we'll go there now?"
She laughed and said, "No Kenny, today was just a chance for us to meet. Email me when you get home and we'll schedule a time for our session." I felt a little stupid after that.
We went our separate ways, and I left feeling enthusiastic about going having an actual session with her, even though she gave off no dominatrix vibes at all. She seemed like just an average woman, maybe even on the quiet side. I emailed her immediately after returning to my car, apologizing for my awkwardness and asking if she still wanted to meet for a session. She responded quickly, saying she thought I was "cute" and she was ready to schedule. I was excited about the idea of a session with Christine, a more "normal" woman than I had ever encountered in my experiences. And the thought of being on a boat was exciting - maybe she would tie me up, and then take the boat out to some private spot on the water, sunbathing on her deck while I sat hidden away, bound and gagged. Or maybe it was a sailboat and I would be tied naked to the mast as she stood at the helm waving happily to other boaters.
We set a meeting time for the next day, and I showed up at the appointed time at the gate to a boat dock. Christine wasn't there, and I waited several minutes, at one point even walking away for a bit so that I wouldn't look suspicious. Finally she appeared holding a large coffee mug, and apologized for being late, saying "I had to finish up some work calls, and I didn't want you to have to sit there and listen." Then as an afterthought, "Though you'd probably like that, wouldn't you?" We walked to her boat and climbed on board. I don't know much about types of boats, but it was large enough to have a lower deck which we climbed down into. This was a relief for me, as there were quite a few people out and about on other boats, and though I had pictured us being out on the deck of a boat, we would have had quite an audience.
There was a sturdy-looking metal chair in the middle of the deck, which she indicated I should sit in. "Get naked," she said offhandedly, with a sip from her coffee cup. And with no preamble, we were getting started. She was wearing a very similar outfit to that of the previous day, if not the same. Right down to the baseball cap, she looked identical to what I recalled of her appearance. I was struck by the normalcy of her demeanor. She bore no visible resemblance at all to a dominatrix, and the deck of the boat, sparsely furnished and a little bit tarnished, had none of the BDSM gear or other trappings I had seen in nearly other experience.
She stood in front of me as I rose from the chair, and I quickly stripped down to my underwear. "Everything off?" I asked, feeling strangely shy in front Christine who was fully clothed.
"No other way to get naked I know of," she said with a touch of impatience. I dropped my boxers, and sat back in the chair, cold metal against my skin.
Christine set down her coffee cup, and knelt next to me, rummaging through a duffel bag I hadn't noticed before. She came out quickly with two sets of very sturdy looking handcuffs. With one look at those, I immediately felt the first stirrings of arousal. By the time she got the first cuff around my right wrist, I was fully hard, which she went out of her way to notice, with obvious approval. She attached one cuff to my wrist, and one to a bar low on the chair, holding my arm down to the side. She repeated the process with my left wrist. These handcuffs looked way more solid than any I'd ever seen before, with heavy silver metal cuffs and a thick chain connecting the two. As she was locking the cuffs into place, I noticed a slight tremble in her hand. Was she nervous? Strange that she would feel nervous, when I was clearly no threat to her now with these handcuffs on. She seemed to follow my train of thought, saying "There's no getting out of my handcuffs." The way she said this gave me a shiver, and arousal rolled through me as I felt helpless and vulnerable. She stood, and watched me for a moment, retrieving her coffee cup and taking a long drink.
She hesitated for a long moment, as if trying to determine what to do next. She had a strange look in her eyes that I couldn't read, like she was really thinking hard about something. I was eager for the session to progress, my mind racing with possibilities of what might come next. Finally she moved to the duffel bag again, retrieving two objects wrapped in bubble wrap. I watched as she unwrapped them, and broke into a cold sweat when I realized what they were. Clamps. Big ones too, not anything like clothespins, these were more like jumper cable clamps but with red plastic tips where the spring-loaded metal came together.
I must have had quite the look of terror on my face, as she smiled reassuringly when she looked at me and said, "Oh don't worry. I tell you what, you get to choose where on your body these go." I was stunned. I couldn't envision any place on my body where these clamps could be applied and not do serious damage. And I had been clear in our initial communications that I was not into pain, and needed to avoid marks on my skin. It seemed I was about to experience both in short order.
"Whoa," I said, "um, I'm... not really into pain, remember?" She looked at me quizzically, then questioningly, as if she didn't remember who I was.
