Chapter 110

I sat back as the woman in front of me panicked. She was not ready for this at all in any way, shape, or form. The thing was that I had things to do and literally didn't have all day. Her fussing all over the room was something that made me want to roll my eyes. She also kept herself to a small area in front of her. The order to play with her son in a fresh new way that didn't only include their love for each other made her hesitate. No matter what she picked up, she looked lost, and I realized a fixable but straightforward mistake I made.

They both didn't know what they were doing when it came to this. I figured I would have had much more entertaining when it came to the young man playing with his mother than the route I chose. That was also why I picked this route. I didn't want the mother getting into the mindset of being the only one to receive. I was planning on doing a perfect job with these two. I want them to spread my name around the city without needing to do it myself. Each time they played with each other in front of a crowd, it would be an advertisement for me. It would be a compelling one the longer they continued to entertain the nobility too.

It was easier to send them back as they are now. Suppose I did so now, though, I could only see them being entertaining to the nobility who grow bored quickly for a matter of months max. Instead, I could train them both to accept even more of each other and kinks they would become much more entertaining. It would even make my client happier if he didn't have to sit on them to make them do something new. I wanted to train these two to want to constantly mix up the type of play they did with each other. It was harder to do this, though, but I had extra days to do so. These two were not like that centaur who probably had problems now thinking of anything other than sex.

I watched the woman fuss, and I knew the reason why she did so. She cared deeply for her son and didn't want to hurt him. She looked at the large metal dildos and restraints with hidden fear. She only wanted to pleasure him without realizing the very act of pain can make that pleasure all the sweeter for him that she can take pleasure in giving him that mix of pleasure and pain.

The concept was too outrageous to her as she contemplated her choices into indecision. If I left her like this, she would forever remain in this mindset. Training her to be able to switch mindsets would be the more difficult part of this training. That, coupled with the fact I would have to have to do that with her son simultaneously, made my work cut out for me. I hid a sigh as I stood up, turning the attention of both the son and mother to me quickly.

"This will be the only time I somewhat instruct you," I said sternly, "I have seen if I leave you to your own devices, you will be here all night." I continued with a chiding tone. Instead of being sad, she looked relieved as I told her that. "Pain and pleasure are the same coin with different sides." I began grabbing a gag. "It can even spice up any pleasure you might feel," I put the gag in her son's mouth, making sure he couldn't say anything. "Your son here would gladly do some play with your body if I gave him the ability to earlier. That doesn't mean that you can do the same at first."

The mother's eyes widened at the admission, "He wouldn't do that to me," She replied to the accusation I leveled on her son, making me snort.

"Yes, he would," I replied with my voice much louder and more confident. The young man pulled on the restraints looking to refuse what I said. "The thing you must remember, though," I began again, "I am doing this as an extra service. IF you and your son want to remain together forever," I shouted, forcing both to listen, "You must be able to do these things to each other. You are both playthings to your Master, and I am your trainer." My tone was severe, trying to make my point to both of them, "Your entertainment and you must be entertaining; otherwise, you will be sold for another reason. I am giving you the ability to be entertaining regardless of how you feel about it." My voice echoed in the silent room as both forgot to breathe. "This isn't only for your benefit; It is for my own too, as I am the one to train you. Nobles will remember that as they watch you fornicate together. You need to keep coming up with different ways to pleasure each other for their amusement. You must be able to accept every part of your training. Not only from me but from each other. I will be gone soon, and you must train each other in various ways not only in private but on stage." I finished before walking over to a cabinet and pulling out whips.

"Pain and pleasure are the same coin, only different sides," I reiterated, "Pleasure your son in the pain. For if you don't, you will lose him feeling much worse pain." I walked over with a riding crop from that cabinet.

I held it out to the young man's mother. She looked at me, lost in thought as she stared at that simple riding crop. Instead of being a simple object to her, she saw a decision. It was the physical object that would change the new dynamic she and her son had reached. I could see the shame as she turned to her son. She had just begun to accept a physical relationship with her son. Now I was taking it to another level. She turned to look at the riding crop and her son several times. The minutes rolled by as I stood still, watching her indecision.

I let her take that time, though. A person willing to learn was what I needed in this instance. I needed her to want to learn, and I would, in time, make her understand her son would too. Still, I could see that faint hope in her eyes that I would pull that riding crop away from her. That dying hope that this was all a dream and she wasn't a slave. That she was at home somewhere in the empire raising her son to be a dock worker or something. And I saw her reach out that hand landing on the riding crop, and that hope died.

I refrained myself as I saw that hope die. It was so beautiful to watch that hope die as she picked it up into her hand. Such a simple action meant so much at that moment, and she killed it with her own hands. To sacrifice so much with such a simple action; Pleasure filled my head, and my already wet pussy moistened further. Still, I kept control of myself as I smiled with restraint.

"W-What do I do?" She asked, her tone firming up. New steel in her spine grew as she killed that old hope. "I never have done something like this. Not to my boy either. I-I-I never even Spanked him!" She exclaimed at the end. I smiled at the naive mother in front of me.

"That doesn't matter," I told her, "You need to learn, and so I want you to use that to hit him. I don't care where I want you to hit him wherever you want." I paused, seeing her horror but that spine still solidifying, "And, I want you to look into his eyes as you do so. I will give you five minutes to hit him ten times. This is such a simple task that if you fail in the next five minutes to do so, I will whip him a hundred times." My order rang out, and the punishment was explicit. The horror at the thought of hitting her precious lover and son rolled through her.

I stepped past to sit down where I had before to watch. She looked down at the crop several times. This woman's indecision was probably one of the reasons she was now a slave, I thought. She looked more and more at it, and time passed. I watched before I said something that truly motivated her. "One more minute to hit him ten times, or I whip him a hundred times," I casually told her like I was asking for a morning coffee.

With a minute left, she looked at me, shocked, and her resolve solidified. The crop moved in her hand finally. I almost let out an exclamation of the time it took for her to do it. I almost had to stop a giggle from coming through with the surprise as she missed her tied-up son. It whooshed by his chest as she went to hit him. She blushed in shame as I held back my giggle I am sure would make me sound like a schoolgirl.

She regained her resolve, though, after a second and the riding crop hit her son. It barely made a noise, and my word was like lightning to her, "Harder," I told her.

The whip moved faster, hitting her son in the chest, and I repeated myself, "Harder or I won't count it next time." This time the crop whistled in the air hitting her son's leg, and he groaned this time. "Again," I told her. The order came out, and the crop whistled. It landed on his hip, and I repeated my order. Soon the count surpassed ten as my voice followed up.

The mother stared into her son's eyes, and her breasts swayed as the riding crop whistled in the air, landing on him over and over. His groans at each hit entered the room as the mother continued to hit her son with that riding crop. The skin on his side began to turn red, and my order to do so again and again stopped. Still, the riding crop whistled in the air as she continued to whip her son with it.

The intensity of the situation as she switched arms to hit the other side. I stood up to watch from the side, and tears dropped from her eyes as she started to whip the other side of his body. They continued that intimate stare even as he groaned after each hit. He now even had a pain boner watching his mother's ample breasts sway with each hit to his body.

I was silent as she started to sweat from the exhaustion from whipping her son. With the tears and the intimate staring, I even began to feel out of place and like a third wheel as the atmosphere turned awkward for me. It spoke to how much these two lovers and mother and son loved each other. I could feel it with their body language, even as one tortured the other. My smile grew as I watched. I had exactly what I wanted, and my voice called it all to a halt.

"Enough!" I almost yelled. My order came out just as the crop was about to land. Her head whipped around to look at me. My sudden interruption took her by surprise, and I could see the tears whip off her face from the sudden movement. There were still plenty dripping down onto her breasts, though. I walked closer, and I smiled, looking at them both. The young man still had tears from the pain dished out upon him from his mother.

I looked down the sides of the young man and realized I forgot to apply the cream for these scars that might develop on his skin. I didn't want to hurt the product after all. Still, I needed to make sure they wouldn't scar. I sighed, looking at that, but I knew I would have to spend more on it. The crisscross of red lines was biting into his skin from the misses his mother hit him with the riding crop. She was an amateur with a riding crop at best. And that was being extremely unfair towards amateurs. Still, she had finally broken through the threshold of doing things to her son. She inflicted more pain than I thought she would in the end.

I turned to the mother, "Take him down and hold him. After each time you do pain play, hold him and help him. He will have a hard time walking; take him to the showers and clean him up." I softly said, "I will get him something for his wounds." I finished.

The mother didn't speak and nodded. I shook my head as she set upon her task without question. Tears blanketed her eyes as she looked upon the damage she did to her son.

I walked away to the storage room. It was a small bottle of regeneration potions. It was heavily watered down but still expensive. I grabbed that potion and brought it to them. I should have used the cream; I wasn't expecting the mother to get so into whipping her son for such a long time. She actually did a real number on his body. It was like she was whipping him while something was being strangled inside of her to death. It was beautiful to watch, and the wet pussy I had was going to make it a pain in the ass to fight tonight.

I made it back, and the woman had gone faster than I expected as I didn't find her in the main chamber. I moved to the shower to see that she was using a towel to help wash his body. The tears still dripped from her eyes, and I almost rolled my own eyes at how dramatic she was being.

I walked in a squatted beside the boy, and helped him drink the potion. It was simple to do, and the mother thanked me for it before I stood up. "Clean up yourselves before I put you back in your cell tonight. Make it quick this is already too many showers for you both today." I finished and leaned back.

My thoughts quickly turned not to the two in front of me but to the expectations I had for Jackie with the Centaur. She better not have fucked it up, I thought with a vicious grin.