Chapter 20: Cheryl's Big Night

I was very excited about Friday night. I had set up as much as I could in advance, and I hope that it did not freak out the Harrisons too much. I rushed home from school, and discovered my parents were already gone. I pushed Girl immediately into service. I had spent half of the night before discussing with her in detail what her role would be.

I finished all preparations by 6:00, and there was still another hour before my ladies would arrive. I paced for a while, and actually considered using Girl to relieve my tension, but decided that would be unfair to Cheryl. Finally, I just took a long shower and dressed.

I looked out the window and saw that Cheryl and Karen were sitting at the curb in Cheryl's car. At precisely 7:00, the doorbell rang. Girl went to answer the door, much to the ladies surprise. She was wearing a maid outfit, of course, but it was more risqué than the previous evenings. She curtsied to the ladies, saying, "Mistress Cheryl, Mistress Karen, welcome. The Master has asked that you follow me."

Girl twirled away, leaving them wondering if she was wearing any panties; following her upstairs removed any doubt. Karen and Cheryl gave each other a look, wondering what was going on.

Girl led them to a closed door and said, "Mistress Cheryl, the Master has left you clothing on the bed. He has instructed me to inform you that you are to wear only what is on the bed. You may use the bathroom to freshen up if you choose to. Someone will be in to retrieve you in approximately 20 minutes."

After Cheryl had entered the room, Girl led Karen to another room and opened the door for her. "There is clothing on the bed for you. The Master has instructed me to inform you that you are to wear those clothes only. The Master will be here in 10 minutes to explain your role in this evening's activity."

Girl then came to me to inform me that everything was ready. I took a deep breath, then I headed down to Karen's room. I entered without knocking, drawing a little shriek of surprise from Karen. She was dressed in the exact outfit that Girl had on.

"What is going on?" she asked.

"You know what is going on," I told her with a smile.

"In general, yes, but why I am in this outfit. And what is the deal with the maid?" she asked.

"Girl is going to be assisting in tonight's festivities," I explained. "As for why you are wearing what you are wearing, tonight is Cheri's night. Your job, as you know, is to prepare her for me. Therefore, tonight you will be her personal maid. Girl will be mine. Girl will tell you what to do and help you in some things. Your sole responsibility is to ensure that Cheri is ready for me, and that she is happy."

"Do you mean that Girl knows what you are going to do tonight?" she asked.

"Girl will assist in what we are going to do tonight," I told her. She looked surprised, but I just continued with her instructions. "You will wait here for another five minutes, while I go downstairs. Then, you will go into the room where Cheri is and say, 'Mistress Cheri, your presence is requested downstairs.' When you say that, you are to curtsy. Do you know how to curtsy?"

"I think so," she said, and she showed me.

"Almost," I said. "A little deeper, lift the skirt slightly higher and lean forward more." I had her practice until I felt that it was right, then I led her in front of a mirror to show her how she looked. When she performed the maneuver, her face turned red as she realized that both her nipples and the lips of her pussy were visible.

"After you bring her downstairs, you are to lead her to the dining room. Then, you are to spend the rest of the meal helping Girl serve and following her directions. When you are not otherwise occupied, you are to stand to the side and behind Cheri's chair, ready to serve her as necessary. Tonight, you are to obey everyone's instructions. Mine, Girl's and your mother's, in that order. Do you understand?"

"Yes," she said.

"Yes, sir," I told her.

"Yes, sir, I understand," she said, curtsying deeply.

"Excellent. I'll see you downstairs."

I proceeded downstairs, where Girl was waiting. She curtsied deeply as well, saying, "Everything is ready, sir."

"Excellent," I replied. We went into the dining room and she held the chair for me to sit down and wait.

Shortly, the door to the dining room opened, and Karen walked in, gesturing for Cheri to follow her. I looked Cheri up and down. Her blond hair was just starting to grow in the back, but was still quite short. She was wearing a white sheath, exposing just a little of her cleavage, but cut so tightly that she could not possibly have worn underwear. I was quite nervous about whether the dress I had selected would fit, but I was pleased to see that it had. Tight around her neck was a single black band with a white cameo in front. I couldn't see it from where I was, but I knew it was of a kneeling slave girl.

I got up as the women entered the room, and I walked over and took Cheri's hands, kissing her on the cheek. "You look absolutely lovely tonight," I said. "How do you feel?"

"Nervous. Excited. I don't know," she said.

"Come," I said, gesturing to her chair. I held it out for her, and she sat down. Girl held out my chair and then poured us each a drink. She then gestured for Karen to follow her into the kitchen.

When they were gone, she asked, "What is going on?"

"That question seems to be asked a lot tonight," I said. "What do you want to know?"

"What is with the maid and Karen?" she asked.

"The maid's name is Girl, and she will be with us all evening. I think that you already know Karen."

"What do you mean she will be with us all night?" Cheri asked.

"Remember when I told you that I knew other submissives? Well Girl is another one. She is a slave, and she belongs to my parents," I said.

"Really?" she asked, seemingly torn between excitement and confusion.

"Really," I told her. "Girl has been with us since I was a baby. She is a complete slave."

"And she is going to be here all night?" she asked nervously.

"She will be participating," I said. "She is going to teach Karen how to prepare you. And she will teach you how to help Karen as well."

The maids came back with the appetizer, and Cheri fell silent. After they served us, they took positions at the side of our chair.

Cheri kept looking at Girl, and finally her curiosity overcame her trepidation. "Girl?" she said.

"Yes, mistress?" Girl replied.

"Are you really a slave?" she asked.

Karen gasped, but Girl said, "Yes, mistress."

"Are you happy?" she asked.

"Constantly, mistress," she said with an encouraging smile.

"Are you well treated?" Cheri asked.

"Of course not, mistress," Girl replied. Seeing Cheri's confused look, she explained, "I am treated as my owners see fit. Well or not, it makes no difference."

"What are you trying to ask?" I inquired of Cheri.

"I want to understand what it is to be a slave," she said in a quiet voice.

"Girl might not be the optimal role model," I said. "My father explained it to me very early. There is not a single type of master or a single type of slave. It is a spectrum. Some people are very dominant. Some are very submissive. Most fall in the middle. Helen, for instance, appears to be a tad on the dominant side." Cheri and Karen smiled at that. "My mother is definitely submissive, but only part way down the spectrum. Girl is very far down the spectrum. She is so submissive that she would hurt herself to obey a command. I think that if you want to get more insight, you'd be better off talking to my mother, or perhaps another woman I could introduce you to. Girl can teach you much, but you have to temper her attitudes."

Cheri looked a little skeptical, so I thought that a demonstration would be in order. "Girl, hold your breath," I instructed. I heard an intake of air behind me. "The problem with listening to everything that Girl says is that she is completely devoted. She cannot or will not comprehend that her opinion, or even her well-being, makes a difference to the commands that she is given. When ordered to do something, she will attempt to carry it out, regardless of the consequences to her. I don't think that you would, or should, go to such extremes.

"My mother, on the other hand, has a carefully defined set of limits with my father. He will push her, but only to her limits. She will not put up with more. Sometimes, they will agree to push things, but it is a mutual agreement. I think, knowing you as I do, that you will definitely want to set limits."

I turned to look at Girl, who was definitely starting to turn red. She was untying the strings of the apron around her waist, so I quickly said, "Use only your own control."

I then turned back to a shocked Cheri and said, "If I had not told her that, she might have tied something around her neck to keep her from breathing, even past the point of unconsciousness. I don't want to hurt her, so I won't let her do that. On her side, she trusts me not to allow her to be hurt. If she were to trust the wrong person, she could be seriously hurt or even killed."

Karen and Cheri were looking behind me in fascination when I heard an explosive expulsion of air, followed by ragged breathing. Girl dropped to her knees and put her head down. "I'm sorry that I failed you, sir! Please punish me!"

I looked at Karen and said, "In the room that you changed in is a dresser. In the top drawer are a number of items. Bring me the whip with the dozen or so strips." She looked at me in surprise, so I reinforced my command, saying, "Now!"

She scampered away, and Cheri looked at me in shock. Karen was back quickly, holding the whip. I took it from her and said to them, "Girl did very well. She does not deserve punishment. But I know Girl, and in her mind, she has failed me. She released the breath before she lost consciousness or I allowed her to breathe. Therefore, she has failed me, and she will be emotionally distraught until she feels she is appropriately punished. It is my responsibility to make her feel better."

I turned to Girl and said, "Girl, punishment position." She stood and bent over the table, raising her skirt.

I stepped behind her and quickly brought the whip down ten times. When I was done, she stood up and said, "Thank you, sir. I'll try harder next time."

She took her position behind me again, as if nothing had happened. I laid the whip next to my plate on the table and turned back to Cheri and Karen. "So when you listen to what Girl advises you, temper it with common sense, OK?"

They both nodded, Karen looking a bit shell-shocked. I finished the appetizer and the maids took away our plates, bringing our soup.

"You look lovely," I told Cheri.

"Thank you," Cheri said. "I love the dress."

"I got it with you in mind," I told her. "Tell me how you are feeling now."

"Scared," she said.

"Good," I told her. "You should be scared submitting to someone. Is that the only emotion that you have?"

"The strongest one," she said.

"Karen, please check to see if Cheri is wet," I instructed. She looked at me in surprise, but then she leaned over, showing me her breasts in the process, and ran her finger up between Cheri's lips. She held the finger up for me to see, and it glistened.

I held my hand out for her to put her hand in, and I pulled it to my mouth. I loved the way Cheri tasted.

"It appears that lust and excitement are pretty strong emotions as well," I said to Cheri. She blushed and nodded.

We ate our soups in silence. The maids cleared the dishes and brought out the main course. I dismissed the maids to go eat in the kitchen, while I talked to Cheri.

"Tell me about the conversation that you had with my parents," I demanded.

"It was weird," she said. "They called me in and your father said, 'We know that you have a relationship with our son. We want to talk to you about it. We will not interfere if we feel that it is appropriate.'

"I asked how they could possibly see a relationship between me and you as appropriate, and he said, 'From what I know so far, there is more of a chance that we will find it appropriate than not.'

"I was surprised by that, and even more so when your mother said, 'Tell me how Jake makes you feel.'

"I didn't know how to answer that. Your mother told me not to worry, just to say what I felt, so I told them. I said that you made me feel taken care of, that you made me feel protected, that you made me feel deserving.

"They asked me deserving of what, and I said love." She lowered her eyes and didn't speak for a while.

"Then your mother asked, 'Does he turn you on?' Your own mother wanted to know if her son turned me on!"

"What did you say?" I asked with a smile.

"I said, 'Yes, he turns me on more than any other person, regardless of age, has ever turned me on. And that is before he had sex with me.'" She blushed again.

"Then what did they say?" I asked.

"They asked me if I understood about being a submissive. They asked me about my history with men. I'm not sure why, but I was completely honest with them. Your mother made me feel really at ease. They asked me what I felt my future with you was. I told them that I didn't know, and unfortunately, I didn't care. I just wanted to be with you."

"Then what happened?" I asked, curiously.

"She asked about Karen. She asked how I felt about the fact that my lover would also be having sex with my virgin daughter. I told them that I couldn't think of anyone I'd rather see her lose her virginity to. She asked if I would be jealous, and I told her that I didn't know, that I hoped I wouldn't be, but only time would tell."

"Then?" I pressed.

"Your mother stood up and said, 'I hope things work out.' She kissed me and gave me her blessing. She said that I was free to come over this weekend, and that she hoped I enjoyed myself, and that I'd better obey you well."

She looked up at me, and tears were in her eyes. "She made me feel welcome."

"She knows what it feels like to be you," I told her. She nodded.

"I think that you will be coming over here to have many talks with her," I said. She nodded again.

We finished eating in silence, though Cheri kept glancing at me with a mischievous look in her eyes. Soon we were done, and the maids came to remove the plates. They returned shortly and Girl asked, "Where will you be having your dessert?"

"In my room," I said. "Please have Karen help you prepare it."

"Yes, sir," she said, and walked to the other side of Cheri. "Please come with us, Mistress Cheri," she said.

"Me?" Cheri asked.

"Of course, Mistress Cheri," Karen said with a smile and a pussy exposing curtsy. "Don't you realize that you are the dessert?"

Cheri looked at me with a smile, then she stood and followed the maids out.

Girl and Karen took Cheri up to the master bathroom. "Remove your clothes, please, Mistress Cheri," Girl instructed Cheri.

She did so, and Girl turned to Karen and said, "You too, Mistress Karen."

"Why?" Karen asked.

"First of all, because you will get messy otherwise," Girl explained. "Second, I believe that Master instructed you to obey my instructions."

"He did. I'm sorry."

Girl removed her clothes as well, and soon all three were naked.

"Now draw Mistress Cheri a bath," Girl instructed Karen.

While Karen was filling the tub, Girl was preparing her task.

"What is that?" Karen asked.

"It's an enema bag," Girl explained.

"An enema?" Karen asked. Cheri looked nervous.

"Master is going to be taking Mistress Cheri's ass tonight. You don't want him to get his cock dirty. So we will clean out Mistress Cheri." She turned to Cheri and said, "Bend over the edge of the tub."

As Cheri complied, Girl told Karen, "Make sure that you grease this very well. You don't want to hurt her." She showed Karen what to do, then put a blob of lube on Karen's finger. "Now make sure that she is lubed inside as well." Karen pushed her finger into Cheri's ass. Cheri moaned, then moaned again when Girl pushed the nozzle in. She opened the valve and the warm water started flowing in.

As Cheri filled, Girl instructed both of them. "If I were you, I would make sure that I was always clean. You never know when he will want to take your ass. In fact, I would make sure that not only was I clean, but that I was also always well lubed. That way, if he came over to fuck Mistress Karen, but he decides at the last minute that he wants to fuck Mistress Cheri's ass, there will be no extra preparation or delay."