Two minutes later, I heard a knock. I opened the door to find her blushing furiously. She walked in quickly, and to my great pleasure, returned to kneel on the floor in front of where I had been sitting.
I sat down, she reached up to my hand and placed four folded pairs of white panties in my hand.
“Good girl.” I muttered as I took them. “So tomorrow. When you are sitting in meetings, and you are wearing your skirt and nothing else underneath, and you have to shift in your chair, you will feel what I did there and what you surrendered to me. The warmth of what my palm has left on your cheek. The absence of a layer of clothing. You will be reminded of what happened here tonight. And what you chose to do.”
A small smile formed on her lips.
“When you look at me, I will know what you are thinking about, what you are feeling. It will be a bit of a secret between us. Would you like this reminder tomorrow?”
She nodded. “Yes sir. I really would.”
“Good.” I checked my watch. “It’s getting late Caroline. We need to be up and ready to go in eight hours so why don’t we pause this until tomorrow night? If you choose to continue, that is.”
She nodded again, seemingly in thought. After a time she then spoke up, “sir?”
“Hmm?”
She nervously looked at me. “Would you like to see what you did?”
I raised my eyebrows. It took me a moment to get what she was asking. “You mean my spanking?”
“Yes sir.” She quickly added, “I mean I know it is not as amazing as what Stephanie . . . ”
“Stop that, Caroline. You are lovely. No more comparing to Stephanie. If I didn’t find you attractive then I would not have pursued this.”
She looked down and nodded.
“Stand up please and turn around.”
She slowly got to her feet and turned with her back to me.
“I would like to see your beautiful bottom, Caroline. Raise your dress for me please.”
She mumbled something, her fingers finding the hem of her skirt. She lifted it in no hurry, slowly revealing her skin. I finally saw her cheeks come into view. I had only slapped her bottom five times total, a few times on each cheek. And it was through two layers of clothing. Even so, I could see the pinkness on each one.
There is something both cute and sexy about a woman’s ass that has been freshly spanked. Her cheeks were firm, her ass matched the slimness of the rest of her body, and I liked it.
I then realized I had likely been quiet too long. Her hands were shaking a little as she stood completely still.
I stood up and stepped close to her. I then reached out and ran my fingers along the skin of her reddened cheek. She reacted by jolting, but then seemingly accepted my touch.
“I love how it looks, Caroline. Apparently, I did well there. And your bottom is lovely.” I could feel the heat under my fingertips.
“You can pull your dress back down. For now.” She quickly did that but stayed in position.
I stepped close behind her. “And one more thing, Caroline.” She didn’t move.
“Do you find yourself aroused right now?”
She paused. I could not see her face. I then heard a softly whispered, “yes sir.”
“I am glad. But tonight, you are not to do anything to address that arousal. You will refrain from pleasuring yourself. Do you understand?”
She actually didn’t speak this time but nodded her head in the affirmative. I am sure things were racing for her so I did not push her.
“Good girl. And before you go to sleep tonight, I want you to text me and let me know that you have been good. All part of your choices, Caroline.”
She paused, then quietly asked, “will you be doing . . . anything tonight?”
I smiled to myself. “Yes Caroline, I most certainly will.”
She didn’t respond.
“Good night, Caroline.”
“Good night, sir.”
She didn’t look back and left the room.
I wasn’t lying to her. I was already hard. And with me holding back from immediately jumping into sexual situations with her, especially as I really wanted her to understand what it was all about, I only had one choice.
I dropped my pants and underwear immediately and “addressed my arousal.” It didn’t take but a few minutes of me stroking a very hard dick as I thought about Caroline across my lap, showing me her pink ass, or even saying yes sir to me. These sorts of outward expressions turned me on in spades.
Watching my hand grip my shaft as I slowly pumped it, well I imagined someone else’s hand there. Or her pussy. Sliding down. Giving herself to me. But honestly, the first time would likely have her bent over a desk as I was quite the fan. Images, anticipation and her all brought me to the edge.
I came into my hand, went to the sink and cleaned up.
I needed to get some sleep but I wanted to review the schedule and the punch list again and contact the office about tasks. I fired up my laptop and worked through some emails.
Twenty minutes later I received a text from Caroline that simply said, “I have been good sir.” I just responded with “good girl.”
I actually started to get hard again.
But then my mind shifted to Steph.
Steph.
I sent her a text — “Thinking about you. Hope you are ok.”
I heard a ding — “me2. :->”
Then another — “ru ‘coaching’ Elsa?”
“Elsa?”
“The IQ”
IQ I knew meant Ice Queen, which of course referred to Caroline. Not sure where Elsa came into all of that.
“Yeah, I gave her some links, and then we talked through it tonight, and did a little experiment.”
“K,” she wrote back.
A few moments later, “go ok?”
I wanted to be honest with her. Above else I cared very much about Steph. But I also didn’t want to hurt her, and Caroline seemed to be a bit of an issue for her.
“Well enough. She is just figuring things out.” I then added, “I think you two should meet. She is curious and you really could help her understand.”
Silence for a bit. Then just one word “sure.”
After some more silence I finally wrote, “heading to bed, Steph. Miss you.”
Quickly the response came, “me 2, B. Nite.”
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