Bondage Sessions: Bondage on a Boat – BDSM

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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 user account of a woman named Christine, whose user account 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 user account photos, I didn’t have a clear idea of what Christine looked like, so I was willing to figure 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 create, 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 wondered 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 start 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 methods, 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 wondered 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 wondered 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 wondered, 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 willing 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.

“Well, what did you think was going to happen?” She said, with a touch of heat in her voice. I squirmed a bit in the chair, really starting to sweat now.

“Well, I thought maybe you would tie me up?” I said somewhat desperately, “Like we talked about?” My statements came out more like questions, trying to determine if she even remembered what we had discussed.

“Hmm,” Christine said, and seemed genuinely perplexed. She took another long drink from her mug. “Well, I guess I could put you in the corner and tie you up…” her voice trailed off as if this were a complete change in plans.

“Sure,” I said “yeah, that sounds good.” I couldn’t be sure she’d heard me, as she had already started pacing around the room. Something very odd was happening, and my nervousness was about to descend into panic. My cock, rock hard moments ago, had completely wilted, she took note of this with disapproval.

She came back toward me with renewed purpose. “What do you really want out of this?” She asked, and then added, “Why did you really come here?”

“Well, just like I said, I’m into being tied up – any kind of bondage and restraint.” It almost felt like I was arguing my case to a skeptical judge. But I wasn’t sure what I was arguing against. And then she said the words that would come back to me over and over, for years after.

“Don’t you ever want to just get fucked?”

After a moment’s hesitation during which I played back those words over and over to be sure I’d heard her correctly. The obvious answer to that question for any man in nearly any circumstance is, “Yes” or “yes of course,” or maybe even, “fuck yeah!” And in the split second I had to decide what to say, if I had chosen one of those options, here’s what might have happened.

She would have smiled, washing away the tension that had built up during the appearance of the hellish clamps, and her odd questioning. It had just been part of the game, a little dominance to throw me off. She would pull off her baseball cap off, freeing her ponytail and rolled her head from side to side. She would then take a few steps toward me, while swiftly pulling her polo shirt over her head, tossing it apart, and revealing a lacy white bra holding up bouncy, large breasts.

As quickly as her shirt was gone, her pants came off as well. Seeing her standing in front of me in her satiny white bra and panties, with me still securely handcuffed to the metal chair, my cock would resume its aroused state, much to her amusement. With another step, off came her panties, revealing a glorious brown bush. She would then close the remaining distance, straddling my legs and sitting on my hard cock, then guiding me into her with her hands.

Overwhelmed by sensations, I would focus on the warm friction as she slowly began move, up and down, forward and backward. She would wrap her arms around my body, pulling her chest against against mine as she kept up her slow movements. She might have whispered into my ear, “be a dear and unhook my bra” then with a playful laugh, “oh, you can’t, can you?” Reaching one hand around behind and unhooking it herself, her bra would be tossed apart, her glorious breasts falling out, bumping against my chest. Pulling against my handcuffs to no avail, my hands would not be free to explore her body, but I would revel in the experience of her complete control and my total helplessness as she rolled her hips back and forth.

On this would go for some time, with her hands groping around my body as she fucked me, exploring my handcuffs, my nipples, my mouth. She would suddenly tense up and tighten around me, and she began bucking wildly on top of me, seeking every atom of pleasure. This would drive me quickly into my own orgasm, powerful and long.

But that is not what happened. I am probably a complete idiot, but I sensed danger in that statement, “Don’t you ever want to just get fucked?” And I said, “Well, I don’t know.” Christine gawked at me, seeming unsteady on her feet as she walked over to me.

She considered my pathetic body, limp and useless cuffed to her metal chair, and said “I’m going to unlock those handcuffs, and it will be your choice whether to walk away right now, with no hard feelings.” She produced the handcuff key, and began unlocking each handcuff. Her hands were shaking noticeably now, and she struggled to get the key into the tiny hole to unlock the cuffs. There wasn’t much I could do to help her, so I watched, still processing what had just happened. It was then that I noticed the smell of alcohol coming from her breath. Strong. And it hit me in that moment, it wasn’t coffee she was drinking from that mug.

She finally got the handcuffs unlocked after what seemed like several minutes of fumbling, during which I started to contemplate that she might pass out, and I might be stuck to this chair for quite a while. Free from the handcuffs, I began to get dressed. I remembered that she had left open the option that we might continue after she uncuffed me. But she had gone from confident and wry to nearly passed out drunk in the space of what seemed like just a few minutes, and my instincts told me I needed to get out of there.

Once dressed, I paused to see if she was gonna walk out with me. She was sitting on the floor, elbows on knees, not looking at me. She waved a hand, possibly to say goodbye, but more a gesture of dismissal, and I found my way out alone.

In the years since, I have often thought what the hell happened in that session. I even reached out to Christine over email once, not with any desire to try again, but simply to find out what her expectations had been, and in what way I had disappointed her. Having never received a reply, the best conclusion I can come to is that she used this avenue as a way to have casual sex, maybe with BDSM aspect as a measure of safety for her. If this was the case, it’s efficient she hadn’t expected to discover genuine BDSM interest in me. It also seems entirely plausible that she was disappointed in what she saw once my clothes came off, and from that point forward she was just looking for a way out. None of that has seemed congruent with the realization that she had clearly started drinking heavily right before our session, and had continued as we progressed. I can not escape the realization that I was in pretty serious potential peril, handcuffed to a chair, on a boat with a person who may have been in a crisis of some kind.

Though one of the greatest disappointments in my exploration of BDSM, my session with Christine has fueled many more “What if…” fantasies beyond the one I wrote here, good enough that they may someday need to be written into story.

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