I paused for just a moment, “but you are curious. The thought entices you, yes?”
She hesitated for a bit again, likely battling this one internally too. She nodded again.
I sipped my wine.
“Why?”
She looked at me with a confused expression.
“Why does that entice you? What draws you to the idea?”
Again a brief pause followed by a hesitant answer. “I like . . . um . . . I like the idea of . . . ” she looked down again as she spoke, seemingly lost in thought.
The way she spoke in these last few minutes was nearly 100% opposite of how she handled herself earlier that day — such confidence and a serious controlled tone had been completely replaced by this innocent-sounding and vulnerable woman, unsure of how to proceed, in a completely unfamiliar and uncomfortable context.
“Eyes on me, please, Caroline.”
She nodded again, her expression both irritated and confused. “I don’t know, Brent, ok?” She even sounded more irritated. No surprise I suppose.
I raised my eyebrow in amusement. “Really? I am quite certain you do know.”
She squirmed some more. She seemed to be having a difficult time with this different dynamic. It felt like a heart versus mind moment for her, maybe.
“I like . . . not being in . . . control . . . I guess.” She finally answered with her eyes looking anywhere but at my face. “I am in control a lot for the job, so . . . ”
I nodded again.
“Makes sense. I can see that. And you excel at controlling things at work, I think.” I sipped my wine. “What were you hoping to find that night?”
She exhaled and then took another sip of wine. Her response came quicker this time. Maybe she finally welcomed the opportunity to process this with someone.
“I . . .” The waitress came at that moment, unloaded the food from her tray, asked if we needed anything else, and upon getting her answer she left.
Caroline immediately dove into eating her soup.
I took a bite of my sandwich. “So you were saying.”
She looked up at me, and then adopted this look of defeat.
“To try it. I guess.”
“So you wanted to find someone who could show you what it was like?”
She paused for just a moment, maintained eye contact and then quietly said, “yes. That is correct.”
I nodded, “I completely understand. And that is a very sensible first step, Caroline.” She nodded a little, maybe appreciatively, maybe just out of habit.
I then turned the conversation away from that topic. The seed had been planted, which of course made me happy.
As we continued eating, I held out my hand patiently, “Caroline, hand me your phone please.” She stared at it for a few moments, then looked at my eyes, maybe searching for why.
“I am going to add my number to it. And I will forward a few things for you to look at. Only things I think would help you in your curiosities, I promise.”
She nodded and slid it across the table. Interesting that she didn’t actually put it in my hand. Little moments of rebellion.
I took it, added my number, then sent myself a text from her phone and handed it back.
She uneasily took it, nodded, and we continued our meal.
I had accomplished what I wanted to do at the dinner, so I let her eat in relative silence, only interrupting her thoughts occasionally with non-threatening casual mundane banter.
We said goodnight in the hallway in front of her room. I returned to my room, answered some emails, prepared a few things for the morning activities, and then retrieved my phone.
I composed my first text to Caroline:
“Evening Caroline. Thanks for a productive day and a pleasant dinner. I am going to forward three things to you: a video where a submissive discusses her experiences in the D/s world, a webpage that discusses the dos and don’ts of Dominance and submission and what is healthy, and an erotic story of a Dom and a sub.”
I then forwarded all three to her.
“Read and watch what you like, but I find these to be good ways to be exposed to this world initially. Feel free to send texts or we can discuss in downtime in the next few days. Good night, Caroline. Rest well.”
I then sent a quick text to Steph to let her know I was thinking about her. And honestly, I was. Steph seemed to pop into my mind at different times throughout any given day, with little pattern as to why.
It wasn’t just the guilt, it was just, well, just because.
We had spoken a few times since me telling her about why I pounced on her the night of the club meeting. We weren’t exactly back to what we were yet, but very close. She had lots of questions about Caroline, and I was all too happy to be transparent with her.
But even so, there still felt to be a little inkling of an unresolved issue there. And I didn’t know what to do.
And with the text sent, I set the phone down and went to bed.
The next day, Caroline avoided talking about the more controversial subject, instead focusing only on work. Safer. But her tone had changed a little — cautious, but with the need to discuss something. Maybe I was just reading into it too much.
At dinner, in the same restaurant, I ordered for her again, she accepted it with a little less silent drama, and we casually talked about the day.
After we covered what went well that day, which honestly was just about everything, I decided to finally head into the topic I was most curious about, “so did you check out any of the resources I sent you?” We were nearly done, so I wanted to get this in before time was up.
She paused, not necessarily anxiously but almost as if she expected the question, and then nodded. “Yes, I did.”
“Any thoughts?”
She paused again. She seemed to need time to reveal things. I was pretty patient so that was completely fine.
“The video was pretty helpful, although I don’t think I can completely identify with her.” I nodded. Caroline being a management type would be a little unique compared to other women in the lifestyle, many of whom were submissive in many, or even potentially all aspects of their lives.
“The webpage was very good, but I think it left me with more questions than answers.”
She stopped for a moment. “And the erotic story was . . . good . . . but again, I did not fully identify with the character. She was younger, not the same kind of work, that sort of thing.” She looked at my eyes, “but it was still helpful.”
Having given her answers, she nodded seriously, “so thank you for sending those.”
“My pleasure.” I smiled at her, paid the check and escorted her to the elevator.
———
We stepped off the elevator and stopped in front of her door.
“Caroline, show me your watch.” She looked at me questioningly but then pulled up the sleeve of her dress and held it in front of me, responding a bit more quickly to my requests. I checked what time it showed at that moment.
“At 8:45, come to my room if you want to know more about the lifestyle. You said you have questions beyond what was sent. I can maybe answer those for you.” She stared at me with the dumbfounded look again. “Caroline, this is up to you. I am not into forcing anything, but if you want to know more, then I offer myself for that. But understand that we play by my rules.”
I paused to look at her seriously then I continued, “We will discuss some general things when you come in, answer questions you might have, things like that, but after that it is about my direction. The offer remains available for you until exactly 9 pm. After that, it is no more. Your choice.”
I raised my eyebrows at her and she hesitantly nodded.
Satisfied, I turned and headed to my door, leaving the hallway.
I could see the shadows of her feet beneath the door long before she finally knocked, one minute before nine.
I opened the door to find her looking a bit panicky, having not changed at all.
I motioned for her to come in, she walked past me quickly and stopped in the center of the room, looking extremely awkward. Her hands literally shook a little at her sides.
I walked towards the chair and sat down, motioning to the bed, “take a seat please.” She sat demurely on the edge of the bed, crossing her admittedly pretty legs, likely thankful for something less awkward, but she still looked very unsure of things.
“So, initially, I was thinking I could answer the questions you have accumulated. Do you have some that maybe you brought with you to the meeting that night? Or that have shown up since reading up last night?”
She nodded her head, the deer-in-the-headlights look never leaving her.
“Um, I guess . . . like how it works . . . I guess. Mostly what I know about this stuff is from movies and well porn. Likely neither of those are accurate.” She averted her eyes at the porn research admission.
She then continued. “The dos and don’ts page was generally useful, but I want to know what it might actually look like, instead of more of a list. Maybe a big picture introduction or something.” Admittedly this uncomfortable and uncertain version of Caroline was pretty hot. The dichotomy of in-control her and out-of-control her felt pretty intoxicating to me.
“Ok. I can do that. Maybe a general overview to start, that can maybe fill in the blanks?” I looked at her questioningly. She nodded so I leaned back in my chair.
“First, many wrongly think that a Dominant/ submissive relationship is all about the control being completely in the hands of the Dominant, or that it is about whatever wish, good or bad, pops into his or her head. This is simply not true. Really the initial power within the relationship ultimately begins with the submissive. Once he or she grants dominance over herself or himself to a Dominant, then the Dominant can proceed. Simply stated, you are in charge of the overall submission. Make sense?”
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