by Jamie Knight
Wearing his silk robe, Jack was stroking himself in a sitting position. He was saying my name over and over. Turning, our eyes met. I was a little shocked at Jack and at myself for violating his privacy. However, he kept staring at me and stroking himself. I didn’t know what to do.
As I stood there like a deer frozen in the headlights, he moaned my name a few times and then came. I didn’t know what to make of it all. I rushed out of the room, got to the guestroom, and locked myself inside. Should I leave? Would he pretend it didn’t happen? I honestly didn’t know.
Suddenly, there was a knock at the door, but I was too afraid to open it.
“Sandra?” asked Jack. “I’m sorry, did I freak you out?”
“A little,” I answered. “I’m the one that should apologize. I shouldn’t have invaded your privacy.”
“You were just curious, but don’t let my fetish turn you away from exploring your own sexuality,” he said. “There are lots of phases to discover.”
“I’m not sure I understand.”
“Exploring your sexuality can be an overwhelming experience,” he said. “But I would like to explore that with you. If you come to my playroom after dinner tomorrow, I will show you.”
“Really? Aren’t you worried about my cousins?”
“Honestly, you’ve been driving me crazy with your outfits,” he admitted. “I know I pretended not to notice, but believe me, I did. You…you’re all I think about.”
“Aww, that’s so sweet,” I smiled. “Tomorrow night then.”
“Yes. Good night.”
“Good night.”
We now had some kind of date planned. Perhaps it wasn’t the open conversation I wanted, but at least he seemed to be coming clean about who he really was. Jack was a complex sexual creature, and I was probably too. He was an explorer in the sexual realm, and he would take me to new heights of pleasure.
I called back Bella.
“Progress,” I reported. “We have a play date tomorrow night.”
“Ooo, play date,” she said. “Sounds interesting. What are you playing?”
“Well, I discovered Jack’s secret sex dungeon,” I revealed.
“What? Get the fuck out of here!” Isabella squealed. “That sounds so badass! Is it full of whips and chains?”
“More chains, fewer whips,” I reported.
“Oh, he is kinky as fuck!” she laughed. “You’re gonna have a great time.”
“I’m feeling a little nervous about it actually,” I confessed. “What the etiquette of this stuff? Like, is there something I should or should not do in these circumstances?”
“No, I would say, go with the flow and whatever you’re comfortable with. Don’t immediately give in if he wants to shove some giant fake Whale wiener in your face. Stand and deliver.”
“Whale what?” I asked.
“Never mind. Just stick to your guns. And if I see that little shit. He won’t get a moment’s peace in this town.”
“Wait, slow down. We’re not even dating yet.”
“Sounds like you got a date tomorrow,” pointed out Bella. “Don’t let that go to waste. When you got a fish on the hook, get the net, and get him in the boat.”
Chapter Eleven - Sandra
All day, Jack had me on edge but in a good way. I was brimming with anticipation now, knowing soon that I would explore the unique passions of his lifestyle. During the workday, he dropped what I saw as subtle hints to what was to come.
“Hey, Sandra,” he said at one point. “Can you process these files for me, or are you tied up?”
“I’m not sure. I have a lot of work already on my plate.”
“Oh, then you sound tied up.”
“I’m sure I can make room for these files,” I replied, with a smile.
“Then you will definitely be tied up,” he added, “with this extra work.”
“It’s no work at all, Jack,” I smiled.
Other than that, it was all business. We went over the merger and the complicated contract. When on camera for our Zoom meetings, it was all very professional. The moment it was off, we would start dropping our innuendos.
“What about this clause of the contract, Jack?” I asked. “Are we bound to it?”
“Not sure. How do you feel about being bound?”
“I rather like the idea.”
“It might be constraining. Doesn’t give you a lot of wiggle room, but I could make it happen.”
“I put my trust in you.”
“You will have to, Sandra,” he responded. “That’s part of the deal.”
We didn’t talk about the lifestyle or what we’d be up to after work, but we talked around it. It was like tiptoeing in a minefield. One slip of the tongue, and it could ruin the game or make things awkward. Certainly, if my cousins heard us, they would become very suspicious about our behavior.
That night, Jack made dinner. It was a beef Wellington with asparagus on the side. I was kind of shocked he had the time, but he kept slipping into the kitchen now and again to work on it. In the end, he removed the sizeable bread-like item from the oven, then sliced it open, revealing the tender beef tenderloin inside.
“Do you understand what it means to be a submissive?” he asked, as we sat at the table. “It’s kind of a specific thing.”
“Well, I understand it means patience and obedience,” I replied. “I’ve always enjoyed taking instructions from a strong, male figure.”
“That’s good. I enjoy the dominance,” he confessed. “But you realize that in some respects the submissive sets the pace. So, who is really in charge at the end of the day? Sometimes you get lost in it. Sometimes, it’s impossible to tell.”
“So, you’re saying the submissive has just as much responsibility as the dominant?” I asked.
“Yes, that’s what a good relationship is,” he explained. “It’s teamwork, even if the power balance isn’t equal on the surface. I find these sorts of relationships more…complicated to explore.”
“It fascinates me,” I said, looking off into the distance. “I’ve been thinking about it for days. Ever since you showed me…the ropes.”
“What’s the kinkiest thing you’ve ever tried in the bedroom?” he asked.
“Hmmm, I suppose, before I met you, nothing,” I blushed. “I’m a virgin.”
Jack’s eyes widened. He smiled coyly. “That’s what it is,” he exclaimed. “I knew there was something different about you. We’ll take this one step at a time, beginning with something easy. We’ll start with a good spanking.”
“That sounds great,” I replied. “I mean, of course, sir.”
“You don’t have to force it,” Jack explained. “The words will come naturally to you after a while. Trust me.”
“I trust you.”
Jack cleared the table after dinner. Without a word, he left the room with me sitting in my chair. All sorts of thoughts ran through my head. Was I handling this correctly? Had I embarrassed myself in this new lifestyle I wanted to try? Would I be a good fit for it? Would Jack accept me, or would my attempt come off as forced?
I genuinely wanted this to work and to be interested. I think I was genuinely curious. My arousal wasn’t fake when Jack had tied me up, so I must’ve liked some of it. I guess it was possible that deep down, I wanted the attention.
Jack was handsome and forceful. Maybe it wasn’t the rope. Could it be that any amount of attention from a handsome man was enough to pique my interest? Would I be bored and jaded with all this in a few weeks or days? Or, would I find deep meaning and sensual desire in the lifestyle?
There was only one way to know for sure.
I looked up at the clock and realized I had been sitting in the dining room for over twenty minutes. Jack had just left me here. Guess I had kind of zoned out thinking about what was to come. And what was to cum.
No instructions? That didn’t seem right. Perhaps as the submissive, I had to anticipate my domin
ant’s needs. Hmm, I was beginning to realize what Jack meant when he said these relationships were more complicated.
I got up but then sat back down. Maybe this was part of a test to see how long I’d wait for him. That was something a dominant would do, right? Make me wait until I was about to burst and then walk into the room. Was I ruining it by getting up so quick? Still, he hadn’t given me any clues one way or another, and we were still in the early stages of this game.
Getting up again, I decided to risk it and go looking for Jack. Walking straight up to his bedroom, I found the secret passage and entered the secret room. Jack was there waiting. He was looking at the door as I entered.
“Come in and close the door, pet,” he instructed. “Then take off all your clothes. Slowly and turn around during the process. I want to see you.”
I did as he commanded, slowly disrobing and letting my clothes fall to the floor. Moving to undo my shoes, he raised a hand.
“No. Those stay on,” he instructed. “Now, walk over to me.”
Moving into his space, I approached until I got very close to him.
“Bend over. On my lap,” he instructed.
Obeying, I did so, but I didn’t lean across his lap. Jack hadn’t said to get on my knees, I bent over near him, letting my torso hang across him.
“You’ve been naughty,” he said. “Haven’t you, Sandra?”
Jack’s hand slapped my bare bottom. The noise reverberated in the room a bit, and the sting made me flinch.
“I’ve been very naughty, yes,” I confessed.
A second slap came, along with his hand lingering on the sore spot and caressing it gently. The feeling made my pussy ache.
“You need discipline,” he said. “Pets need constant supervision. It’s the only way they can properly function. Do you not agree?”
“Of course, sir,” I agreed.
My position over him made me a little unbalanced. As he spanked me with his open hand, I was threatening to teeter over on top of him.
“Don’t fall,” he said insistently. “I would be very disappointed if you lost your balance just now.”
“Of course, sir,” I acknowledged in agreement. “I’ll do my best.”
“Your best?” he scoffed.
“I will succeed,” I corrected. “I shall not fall.”
“Good, that’s what I want to hear,” Jack responded. “I think I would like to add some light bondage to this. Would that be acceptable to you?”
“Of course, sir,” I agreed. “I’m sure you know what’s best.”
“Don’t move.”
He stood up and left me hovering there. Walking to a drawer, he opened it and found what looked like some red ribbon. He wrapped it around my wrists and then tied the other end to his chair, which he now positioned in front of me.
I had been bending over for several minutes. The strain was beginning to take its toll on me, but I tried not to waver. Jack suddenly spanked me with his open palm again unexpectedly. I let out a surprised squeak and almost laughed, but I bit my lower lip and kept it inside.
Behind me, he would spank and then rub. Pain and then pleasure. His fingers drifted, finding themselves rubbing my bare pussy lips and asshole. I could hear his heavy breathing as he gently stimulated me. Then Jack began rubbing up against me with the bulge in his pants.
“I…need this,” he said breathlessly. “I want to penetrate you.”
“Do it, sir,” I responded, almost begging. “I want you inside me. Take my virginity.”
I could hear him furiously stripping off his belt and pants. Now I felt his bare cock, already erect, rubbing up and down my butt crack. It felt huge. He teased my hot pussy with the end of his dick. I kept myself bent over as before. I was getting shaky but still managed to stay in position. Jack reached down and untied me from the chair but kept my wrists bound.
“You may steady yourself on the chair,” he announced. “You may have to.”
I grabbed the back of the chair just as I felt him insert his dick in me from behind. His hard cockhead spread my walls, and I let out a gasp.
“Yes, sir,” I whispered. “Please make me a woman.”
After a little pinch, Jack slipped in easily. His foreplay had made my insides dripping wet. In and out, in and out, his thick cock started to work my pussy. His thrusts became more and more intense — almost animalistic.
Suddenly, he grabbed me by the hair and pulled my head back a little. Now he was railing me furiously and breathing and grunting. I put both my hands on the chair, trying to use it to steady myself as he pounded away. It was a glorious feeling. My pussy walls being spread, and the pumping of his engorged cock inside me.
Jack took me by the hips. He pulled me forward as he thrust inside me as deep as he could. I was shaking from the experience. My pussy was so wet, and I could feel tiny little orgasms building up to something bigger.
“That’s it,” I tried to say. “Oh, God, yes, Jack. Fuck me like that! Please! Don’t stop!”
“You like this cock, huh?” he asked, panting all the while. “You like this cock deep inside you?”
“I love it!” I cried.
“You want me to cum inside you, don’t you? Say you do!”
“I do, sir!” I cried. “Please cum inside me! I’m begging you!”
“Here it comes!” he grunted. “Coming…inside!”
I could feel him explode into the condom. His warm cum filled me with a sensation that sent me over the edge. Coming on his cock, I was shuddering from a standing position. My legs were almost numb at this point. I honestly felt like I was going to just collapse. Somehow, I managed to stay standing, partly because Jack steadied me with his two hands as quivering took over my insides.
“Ooooh! Oh!” I exclaimed. “Ooooh!”
I had lost my ability to talk. All I could do was make appreciative sounds and try not to fall on the floor. Jack spasmed inside me a couple more times, then slowly pulled out. For a moment, he left me standing there, still steadying myself with the chair. I heard him pull up his pants and get dressed.
Then, unexpectedly, he picked me up in his arms. I felt his broad, muscular shoulders caress me as he carried me into the bathroom just off my bedroom and set me in the bathtub. Still shaking from the experience, Jack exited the room, leaving me there to process all the sensations I was feeling.
I didn’t see him for the rest of the night. Was this a signal that I should clean myself up after our session, or was he just setting me some place where I wouldn’t make a mess? He left me sitting there, wondering what would happen next.
Chapter Twelve - Jack
What was I doing? I never should’ve gone down this path with Sandra. I swear, I’m going to end up in an HR thing, kicked out of the firm, losing hundreds of thousands of dollars in court. Why couldn’t I just walk away from her?
But I knew. I knew the moment I invited her to this house that it would happen. Maybe I even knew it the moment I saw her. This girl was different. With the other women, I had been in control. I had been in such power that it eventually became boring for me.
With Sandra, I would be in control of her for a while, then lose control of myself. It was scary and exciting at the same time. The risk was tremendous, but so was the reward, which was why I was anxious to do it again.
I should just send her packing. If I sent Sandra home right now, this would all end. Sure, she’d be hurt and confused for a while, but ultimately, I’d get back my control. I could tell her that I was no good for her. Make is sound noble. With my hold over her, I could sell it. Then I wouldn’t be endangering anything. The firm would be safe.
The next day, I concentrated on work and remained distant from Sandra. She couldn’t tell if I was mad at her, busy, or what. She’d attempt to start banter or innuendo with me, but I would ignore it or be unresponsive. It frustrated her to no end, but it also, I think, may her more determined to reach me.
I felt a little ba
d about it. The whole act felt mean. By the end of the day, she’d be squirming, wondering if I had changed my mind. She probably thought I would send her away. I certainly was giving off that vibe.
Maybe I just needed a night away from her. If I slept alone, I could work out things in my mind, in the dark, while lying in bed. It was meditative. I’d be calm, and there’d be no pressure to interact with Sandra. Then I could step back and get some perspective on what I was doing.
At dinner, we ate in silence. Judging by the way she was looking at me, I think Sandra was anticipating something was going to happen. She cleaned up the dishes, and as she did, I slipped out of the dining room. I immediately when up to my room, got undressed, and went to bed. I had been so stressed out from running the scenarios in my mind, I quickly fell asleep.
When I awoke, it was dark outside. It was a little after midnight, and I felt refreshed. Perhaps now I could work out in my own mind how to proceed with Sandra. That’s when I noticed the light coming from the bottom of the door to my secret room.
“Oh, no,” I said aloud.
I got up and went inside. Squinting in the light, I found Sandra sitting on a leather bench. She had tied down one of her hands and was using the other to stimulate herself with the vibrator.
“What are you doing?” I asked.
“Trying to tie myself up,” she admitted. “It’s not the same. Will you do it?”
“Sandra, look—”
“Please, sir,” she said, looking up at me with her big doe-like eyes. “I need to be taught.”
She handed me a riding crop, and I gripped it in my hand. Then she got up on all fours on the leather bench. Her robe fell open, exposing her bare bottom. She was prepared for another spanking.
“Like this, sir?”
It was her calling me “sir” that did it. Sandra was slowly becoming the perfect submissive pet for me. Despite the trouble I knew it would cause, I dove in. I secured her hands on the bench, pulled her robe the rest of the way back, and started slapping her bare buttocks with the riding crop. Soon her cheeks were pink and a little swollen.