Switch, Ch. 02

Story Info
And then it continued in Chicago . . .
8.7k words
4.83
4.1k
4
Story does not have any tags

Part 2 of the 3 part series

Updated 06/16/2023
Created 05/15/2023
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

Simon Says: Read Chapter One for the actual context here. Not a stand-alone piece. One more chapter after this. Happy reading.

-----

"Seats 3A and 12B."

"Ok."

Caroline handed me my ticket to board the aircraft.

As the project had drawn to a near close, the client had been very insistent that the project leadership -- ie, Caroline and me - travel to Chicago to meet with them. Caroline had sent me a simple email the previous Friday to be ready to go for four days to Chicago, leaving on Tuesday morning. We were supposed to be in Chicago in their offices by 10 am.

We met at the airport very early, with Caroline showing up with one minute to spare before the flight boarded, and so we boarded together. But somehow she had managed to have our seats reserved so we would not be sitting together. This amused me to no end and gave me such a jolt of pleasure. This meant without a doubt that she had been and still was uncomfortable and that she did not want to discuss anything.

It had been weeks since I saw her at the meeting, and each day it got more interesting to me as she appeared increasingly more uncomfortable at each encounter. She had not been able to shake the experience either. Of course, I could have just confronted her in the office, but that would have invited passers-by to hear about another side of not only her but also myself. This trip was actually what I needed.

This made the chase a bit more exciting.

"Which one do you want?" I was walking behind her with my overnight carry-on.

"I got 12B."

I shrugged. "3A it is. See you in Chicago, Caroline."

"Yea." She quickly scooted back the remaining rows to her seat. I managed to see that not only did I not have a seatmate, but she didn't either.

I smiled at her as I sat down. She quickly averted her eyes. Yep, the chase was getting exciting.

The flight proved uneventful. She barely acknowledged me as we went through the airport in Chicago. I decided to let things simmer so I didn't mention anything in our little moments where it was just the two of us. Not enough time to really delve into it anyway, and I wanted to make sure when it was discussed it was not interrupted.

She seemed more tightly wound than usual. She of course had been in the office, but it felt like she was concerned that with so much time together she was in danger of having to finally face it. While she tried desperately to avoid me at the office, she couldn't do it here. She finally had to face how she felt about the world I spent my time in. This just fed me.

We met with the client all day, meeting after meeting with various project stakeholders. Several more final working meeting days would follow with us traveling home on Friday afternoon, as the client anticipated a late Friday wrap-up. The final day, Friday, we were to meet with their project staff separately and their CIO for bigger picture discussions and next phases of the project, which always made my bosses happy to get a view of future work, which of course meant more money.

As I acted as the technical lead, clients often discussed these things pretty openly with me as they knew I wasn't trying to sell them anything. In fact, the CIO likely wanted to get a "free" hour of technical advising and brainstorming. Frankly, I lived for that kind of stuff so I was looking forward to it. Chances were, Caroline was going to sit in and take notes, which of course the longer the list the happier our sales execs were going to be. They weren't invited to Chicago for these client meetings so they really couldn't work their voodoo. It all depended on Caroline and me.

She managed to arrange a one-on-one with her counterpart at the client for lunch, so we went our separate ways on the first day. I usually liked to work during lunch so that was fine.

As the last meeting of the day came to a close, I had thought about things with Caroline all day, and so had built up a little excitement over how I could handle things with her. Tonight. It was going to be tonight. Let's see how she reacts.

We arrived at the hotel. It was pretty nice, all on the client's dime. Before Caroline could do it, I grabbed her bag. She gave me a brief dark look but then just followed me in.

We checked in and headed up to the fourth floor where both of our rooms were.

"Let's grab dinner, Caroline." She was at her door and I was at mine, three down from hers.

"I think I am going to just . . ."

"You need to eat, Caroline. Plus the client is paying for it, so let's meet downstairs in thirty minutes and grab food at the hotel bar. I checked it out and they have decent food there. And we can discuss today and what will happen tomorrow."

She got ready to open her mouth again, so I just interrupted.

"Great. See you in a bit." And with that I opened my door and headed in.

I headed down twenty minutes later. I was setting the pace so I wanted to get there ahead of her.

I had ordered a bottle of wine, light and fruity. The table had been set, as it were.

She walked in about ten minutes late. She looked around with a little uncertainty and then eventually met my stare. The déjà vu was not lost on me, and maybe not lost on her either. I smiled. She eventually began walking towards me.

She had not changed out of her dark gray heather sheath dress. Her sandy blond-ish brown-ish hair had been tied into a ponytail.

I stood up and pulled out her chair. "Glad you didn't bolt back out the door."

She actually blushed and averted her eyes. She apparently had been thinking the same thing.

She opened her mouth to speak but I continued, "I took the liberty of ordering wine for us."

She nodded as I poured.

I had discovered over time that I loved taking control in situations like this. It was a bit of a game to me. And she was acting as I thought she would: she was NOT in control, she was in my hands, and so I was running things. And if my guess was correct she may be secretly deep down loving it. Maybe.

Tomorrow, she would be running the meetings and such so the dynamic would shift again. But what excited me was the thought that even though she would be "managing " things, secretly she would be remembering moments like this. Moments where she relished in giving up control to a person who knew exactly what he wanted.

And at that moment I certainly knew exactly what I wanted.

"What are you hungry for?" I casually pushed the menu across the table to her.

Apparently she welcomed that escape from having to deal with me. I sat and watched her look at the menu. She put it down and just stared at me.

"Well? What are you going to have?"

It looked like she really struggled as to whether she wanted to give me this information. I knew what was going on in her mind. The little internal battle sometimes proved the most satisfying initially, and most impactful in the long run.

I continued to stare, waiting. She sighed and gave in.

"A half turkey club sandwich and whatever the soup of the day is."

I nodded.

The waitress came over at that point and smiled at Caroline. "Hi. Welcome to the Tavern. I am Tami." She then turned back to me. "Ready for some food?"

"Yes, what is your soup of the day?"

"It's a creamy carrot soup, sir." I glanced at her, "would that be ok?" She stared at me. She was thrown off-kilter again. And then seemingly not sure how to handle it, she nodded.

"Yes, she would be fine with that. Also she would like a glass of water and a half turkey club sandwich." Before the waitress could respond, I added, "and I will take a Reuben."

"Very good sir." And with that the waitress left.

"So how did you think today went?" I casually took a sip of wine, silently enjoying her trying to process what was happening.

"Oh. . . yeah . . . I think the groups were happy with everything, especially the operations side. The customer care department seemed to have some longer term goals. Robert will be happy because it will likely lead to more work. Happy customer and all that." She paused, slightly awkwardly, "you?"

"Sure. The people on the ground loved everything. IT is having a heyday. Their lives just got a lot easier, that's for sure. The punch list of changes is small. We can have that done before we even leave Chicago on Friday afternoon. I sent John the list before we left the client's this afternoon and he apparently already started working on it immediately. He seemed confident it would be addressed quickly."

I shrugged, "so one day down and everyone is happy. Just need to survive three more. But honestly, Caroline, I have a very good feeling about this project and this client."

She nodded in agreement and sipped her wine. We sat quietly for about a minute or two. Her eyes seemed to avoid meeting mine. I found myself relishing in the amusement of it all.

"So, let's talk about the club meeting, shall we?" I threw it out, mostly to see how she would react. I had hoped it would make her a little more uncomfortable, not because I enjoyed seeing her suffer but really because her being uncomfortable about it confirms what I had been assuming about her interest in such things.

And she didn't disappoint. Again. She froze, looking like she was trying to figure out how to get out of talking about it.

I didn't wait. She was answering my questions just fine by squirming.

"Have you actually ever been in a Dominant and submissive relationship before? Or were you just curious that night?"

Deer in headlights. I waited.

"I . . . " She started. Maybe she was hoping I would jump in and save her, but I didn't. I wanted to hear the answer, waiting for what felt like five full minutes of silence.

I think the fact that she needed to answer finally dawned on her and she sighed.

She then just mumbled, "curious."

"So you never have tried anything like that before?"

She shook her head. Her eyes kept moving down, averting her gaze.

At some point I anticipated that she might be more comfortable with this. It just wasn't yet.

"Look at me Caroline." Her eyes came straight up, almost automatically. "Good." She continued to look at me, but even the word 'good' spoken seemed to almost make her wince. Internal battles.

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?"