Chapter Sixteen: Karen's New Job
Karen sat down with me at lunch again. "Why aren't you fucking my mother?" she asked.
I looked up at her in surprise. "Last time you asked if I was fucking your mother, now you want to know why I am not?"
"She needs it so badly," Karen replied. "It's cruel not to help her."
I decided to shift the conversation a little bit. "Did you do anything interesting last night?"
She blushed and lowered her head. Then she looked all around and said, "I can't talk about it here!"
"But we can talk about me fucking your mother?" I asked.
She shook her head.
"So you're not going to tell me about last night?" I asked.
"I..." she started. She looked around and asked, "Do you really want to know what happened?"
I nodded my head.
"Come over after school, and I'll tell you," she said, then she picked up her lunch and went to a different table.
After school, I stopped by to talk to Karen. When I knocked, Cheryl answered the door, then smiled when she saw it was me. She was wearing a white, button down shirt, tied under her breasts and unbuttoned, so that her tits were pushed up and the tops were visible, and a short white skirt barely covering her bottom. When the door closed behind me, I pulled her in for a kiss. When I was done, she didn't want to move away.
"Did you have a nice night, last night?" I asked.
She blushed and said, "It was interesting."
"Is Karen home? I wanted to talk to her."
"Did you do anything to her?" Cheryl asked.
"What do you mean?" I asked.
"You'll see," she said. "She's out by the pool."
We walked out to the pool, and I saw what Cheryl meant. I was used to seeing Karen in conservative, one piece bathing suits. Now she was clad in one of Helen's skimpiest bikinis, her white stomach a stark contrast to her tanned arms and legs. When she saw us, she looked extremely nervous, her hands fluttering around her stomach as if to cover it up. She should have been more concerned with her breasts. This suit had to be tight on Helen, and Karen was bigger up top. She was bulging out of it.
"My, my, this is quite a different look for you," I commented.
"Do you like it?" she asked nervously.
I smiled and said, "It's lovely on you, or rather, you are lovely in it."
She smiled and dropped her hands to her side.
I turned to Cheryl and said, "I need to talk to Karen in private. Leave us alone for a bit."
"Sure," she said, starting to move away.
"Oh, Cheryl, I just wanted to say that that is a very nice shirt."
"Thanks," she said with a smile.
"Can I have it?" I asked.
"What?" she asked, confused.
"Can I please have your shirt?" I repeated.
She looked confused for just a second, then got a sultry smile on her face. "Certainly," she said, as she slowly undid the knot under her breasts. She arched her back as she slipped it off her arms, then walked up to me and dropped it in my lap.
"Call me if you need anything," she breathed sexily, then strutted into the house, topless, under the gaze of me and her daughter.
"Ready to tell me about yesterday?" I asked Karen, surprising her.
"Um, sure," she said.
"Start with the conversation with your mother," I instructed.
"OK," she began. "It was hard to talk about it, but you told me that I should. I told Mom the same thing that I told you, and she started crying. I asked her what was wrong, and she said that she didn't realize that she'd been so unhappy. Then I told her that I thought that I was the same way. She said she understood, so I asked her what she understood; what was she like, how did she feel and did that mean that I was like her?
"She said that she didn't know, but she said she'd try and tell me about her. So she told me that she likes ... to be bossed around, I guess. We talked about it, and how she was unhappy because no one but Helen was bossing her around, and she felt bad that Helen was, because she was supposed to be the mother.
"Then I asked if you were bossing her around, and she said yes. I asked if you were having sex with her, and she said no. The funny thing was, she sounded really disappointed. I asked if she wanted to, and she said yes. Well, not like that. She said, 'God, yes!' like if I had asked one of my friends if she wanted to date a rock star.
"I asked her why she liked having you boss her around, and she said that she couldn't answer that, it was just the way she was. She asked if that was what I meant when I said that I was like her, but I said that I wasn't sure."
Karen went quiet for a minute. "You aren't sure if you want to be bossed around?" I asked.
"I just don't know. I know that I don't like bossing people around, but I just try and stay out of people's way."
"How do you feel when people tell you what to do?" I asked.
"What do you mean?" she asked.
"Helen, for instance," I replied. "What does it feel like when Helen demands something from you, and you do it?"
"I don't know," she said quietly. "I guess it feels like I have to."
"Do you get any satisfaction from doing it?" I asked.
"I don't think so. Maybe," she said. I clearly wasn't going to get too far with this line of questioning.
"So why did you ask your mother to let you watch when I fucked her?" I asked.
Karen blushed when I said the word 'fuck', but she just shrugged. "I don't know. It was a spur of the moment thing. I didn't think she'd even take me seriously. I just wondered what it would be like."
"Haven't you ever had your own boyfriend?" I asked.
"No!" she exclaimed. "Boys don't like me!"
"Then they clearly have never seen you in that bikini," I said.
She looked down at herself and blushed.
"If they were to see you like that, they'd be struggling to keep their hands off of you," I said.
"What about you?" she asked.
"What about me what?" I replied.
"Are you struggling to keep your hands off of me?" she asked, looking extremely vulnerable.
"Your mother is inside topless," I said. "I could have her come out here and fuck her right now. And nevertheless, I am desperately struggling to keep my hands off of you. I keep thinking, 'She must look fabulous out of that top.'"
Karen looked at me intently then sat up, reached behind her, and pulled her top off. Her breasts were fabulous. Just slightly smaller than her mother's, with absolutely no sag, and beautiful, light pink nipples.
"If you want me to have a serious conversation with you, you'd better put that top back on, because I sure as hell am not thinking with my big head right now!" I told her.
"What will you do if I don't?" she asked.
"What do you mean?" I replied. I had been honest with her, and I wasn't thinking completely rationally.
"Will you punish me? Mom told me that if she misbehaved that she would be punished. Are you going to spank me if I don't put my top back on?"
"Is that what you want? Do you want to be spanked?" I asked seriously.
Her expression became less confident as she said, "I don't know. Aren't you supposed to know what to do?"
I laughed. "You think that I know what I'm doing with your mother? I'm just trying to stay a step ahead of her. I know that she needs more than she is getting, and I'm trying to satisfy that need, but if you think that I know all her deep, dark secrets, and I am going to do everything right, then you are wrong.
"Karen, your mother is submissive, and I know a bit about dealing with that. I can guess how she wants to be dealt with, and I am moving slowly to see what she likes and what she doesn't like. With you, on the other hand, I don't think any of us know what you want, so I'm not sure what to give you."
I sat back and asked her again, "Why do you want to watch me with your mother?"
"I want to see what its like," she told me. "I want to know what it's like for her. For you. I want to figure out if it is what I want, too." She was quiet for a moment, then looked up at me. "I want to see my mother punished."
"You think that I will punish her?" I asked.
"Isn't that why you are going to fuck her in the ass?" she asked, surprised.
I laughed at her. "No, Karen, I am not fucking her in the ass to punish her. I am doing it because she has never had it done, because she sees it as a very subservient notion. She is giving me what she has never given anyone else. I am having her prepare herself so that when we do it, it will be pleasurable for her. In fact, I am thinking of allowing you there, because that will make it more pleasurable for her."
"It will?" she asked.
"Yes, because she doesn't think she wants you there, and she will feel more submissive for allowing it. But what about you? What are you going to be doing while I am taking your mother?"
"What do you mean? Just watching," she said.
"Really? It will be like going to a play. You'll sit in the audience and be able to just watch, unaffected? Shall I get you some popcorn?"
"I don't know," she said. "I guess I never thought it out."
"How did you feel last night?" I asked.
"Last night?" she repeated, with a blush.
"I assume that your mother asked to speak with you in her room last night," I said. "Is that what happened?"
Her blush got redder and she said, "My mother did ask me to come into her room last night."
"And what happened?" I asked. She looked at me, like a deer in headlights, but I just returned her gaze, so she started telling me what happened.
"I had asked my mother whether I could be there when you took her," she began.
"Is that really what you asked her?" I inquired. "Because the way I heard it was a little different."
"I guess that I asked her to find out from you if it was OK for me to be there," she replied.
"Why have her ask me? Why not just ask her?"
"Because she told me that you were in charge. I knew that you would be the one to make the decision," she told me.
"It's not that great a leap, but many people wouldn't have made it," I told her. "I think most people wouldn't have internalized the fact that your mother was not going to make the decisions, especially with someone as young as me. Even though she'd said it, most people would have assumed that she at least had that much control. Why do you think that you got it?"
She just shook her head, but her eyes were on the ground, and I think that she knew the answer. I let her off the hook.
"So what happened after you asked your mother to ask me?" I inquired.
"I guess that she did, because later that night, she called me into her room. She said that she had talked to you, and that you said maybe, but there was a condition." She paused momentarily, then continued. "She said that if I were to see her get ... fucked ... then I should be able to see her do other things.
"She was wearing a robe, but she dropped it, and she was naked underneath. Her ... pussy ... was bald. I said, 'Mom! What are you doing!', and she told me that she was following instructions."
She paused again, then looked up at me and asked, "Do I really have to tell you the rest?"
"Are you asking me if I am going to make you tell me the rest?" I asked.
She looked sharply at me and gasped. I glanced down and saw that there was a spot on the front of her bikini bottom. She saw where I was looking and she closed her legs so that it was not visible. She looked up at me and said, "Yes. Do I have to tell you the rest?"
I leaned forward and put my hands on her knees, spreading her legs far enough apart so that I could see the wet spot. I looked into her eyes and said, "Yes, Karen, you must tell me what happened in your mother's bedroom."
She nodded, took a few deep breaths, which incidentally did lovely things to her naked chest, and continued. "Mom laid down on the bed and pulled some things out from under her pillow. She spread her legs and I asked why she was bald down there. She said, 'Because Jake told me that's what he likes.'"
She looked at me again, her legs spreading a little farther and asked, "Is that really what you like?"
"Yes, it is. Is that a problem for you?" I asked.
She looked at me, then with another deep breath, she stood up and pushed her bikini bottoms down. She sat back down and looked at me with a determined expression on her face as she spread her legs to where they were before. I glanced down and saw her moist, pink lips, and surrounding them, smooth skin, as hairless as the day that she was born.
She continued relating her activities as though nothing had happened. "Mom picked up one of the things on the bed and said, 'This is a butt plug. It's small, but I'm using it to prepare for when Jake fucks me in the ass.' She looked me right in the eye when she said it, and she sounded so proud.
"She took a bottle of oil and poured some on the plug, then on her fingers, which she put in her ... hole. She said that she needed to get it all oily so that it wouldn't hurt. Then I watched as she pushed it in. It looked like it hurt, and I asked if it did, and she said, 'A little, but mostly it feels full. Jake is bigger, and if he doesn't feel like it, he won't be so gentle, so I need to make sure that I am ready for that.' I asked her if she had seen you, and she said that she had, that you had jer... masturbated on her." I nodded.
"Then she took the other toy, a dildo, and she put it in her ... she started ... fucking herself. She looked at me for a little bit as she did it, but then her eyes closed, and she started whispering your name."
"She was whispering?" I asked with a frown.
"At the beginning she was," Karen informed me. "Then she started talking louder. Actually, it wasn't really talking, it was more like chanting, or begging. She kept saying, 'Please, Jake, please fuck me. Please fuck me in my ass.' It was really quite embarrassing." She paused for a minute, then looked back up at me with a lopsided smile. "Almost as embarrassing as sitting in front of my mother's ... master, stark naked ..." She looked down at her crotch and continued, "And dripping."
I glanced down, and her lips were puffy and wet.
"Why are you sitting in front of me naked? And dripping?"
"Don't you want me like this?" she asked, unsure of herself.
"Of course, I do," I told her. "But so does every boy in our school. I don't see you spreading yourself naked for them. Why did you do it for me?"
"I don't know. It seemed like the right thing to do."
"What was the right thing to do?" I probed.
"Offer myself to you," she said, blushing again, her legs closing.
"Are you offering yourself to me?" I asked gently.
"I'm not sure," she said. "I didn't really plan any of this except the bathing suit."
"Well, I have to say, I've never had a better offer," I told her. She looked at me in surprise as I continued. "Unfortunately, much as I'd like to take you up on the offer, I don't think either of us are ready for it. Yet."
I paused for a moment, still looking at her. I glanced down between her legs, and when she saw where I was looking she spread them again.
"So you want to be there when I take your mother?" I asked.
She nodded.
"Well, what if I say that you can join us, but you have to participate?" I asked.
"Participate?" she said, and I saw her exposed nipples get even harder. "How?"
"Maybe I'll have you prepare your mother, then get me ready, then have you guide me in. How would that make you feel?"
A flush spread across her chest and her breathing quickened. "You wouldn't really make me do that, would you?"
"Why not?" I asked.
"How can you make me get my mother ready to be fucked?" she demanded.
"Why not?" I leaned forward again. "Maybe I should put you in charge of ensuring that your mother is always ready for me?"
"You wouldn't!"
"Why don't we try it now?" I asked.
"What do you mean?"
"I'm going to go into the den. You go inside and ask your mother where she keeps her dildos. Don't let her talk about anything else, including the way you are ... dressed, other than to answer your question. When you have an answer, go upstairs and pick one out. Then go back to your mother and take her skirt off. Don't have her take it off, or tell her to. You take it off of her, hand her the dildo, and tell her to come to me in the den."
"What should I do afterwards?" she asked.
"I want you to come to the door of the den and stand there until I give you other instructions," I told her.
"OK," she said.
She got up to go inside, and I saw her ass wiggle as she walked. I stopped her before she got to the door and I said, "You forgot something."
I picked up her discarded bikini and walked over to her. I handed it to her and said, "I want you to fold this up and put it on Helen's pillow."
"But it's dirty, and Helen will know that I wore it!" she complained.
"Yup," I said.
She took it, nodded, and went inside. I followed, but went and made myself comfortable in the den. It would be a few minutes until the next act.
Cheryl walked into the den, stark naked and carrying a large dildo. I got up and gave her a kiss, pressing her naked body to mine. "Sit down, I want to talk to you for a bit," I said.
She sat in a chair across from me, with her back straight, maybe even arched, and her legs spread a bit more than hip distance apart. She was clearly posing for me. I glanced behind her at the door of the room, and there was Karen, also nude, leaning against the doorframe, posed, but unconsciously so.
"What did you do to my daughter?" Cheryl asked me, though her tone was non-threatening.
"Which one?" I asked playfully.
"The one that I left you chatting with by the pool. The one that came in, stripped bare and clearly excited. The one that demanded to know where my toys were. The one that came back with this and proceeded to strip my skirt off without so much as a by-your-leave. The one that demanded that I come in here to you. That daughter."
"I just had a little chat with her," I said, looking up at Karen to see that she was blushing.
"Are you going to fuck her?" Cheryl asked.
"Do you want me to?" I countered.
"Ummm," Cheryl stammered. That was clearly not a question that she was expecting.
"What are you more interested in? Whether I'm going to fuck Karen, or whether I'm going to fuck you?" I asked.
She dropped her eyes and said, "Me."
"What if I said that you'd have to help me fuck Karen before I fucked you? Would you do it?" I asked, looking at Karen's surprised face. Her mother nodded.
"What if Karen didn't want to? Would you convince her?"
"I don't know," she said quietly after a long pause.
I sat back and changed the subject. "How has Helen been treating you?"
She took a moment to get her mind on this new track before she said, "Similar to before. She demands that I do things for her, she won't listen when I tell her to get off the phone. She demands that I take her places and buy her things."
"Do you feel the same as you did before?" I asked. She shook her head.
"What is different?" I asked.
"She is doing it knowingly. She knows that what she is doing excites me, and she teases me about it."
"And how does that make you feel?" I asked.
"More excited," she replied.
"Has she made you do anything sexual?" I asked.
"No!" she exclaimed.
"Would you do it if she asked?" I inquired.
She thought for a minute, then nodded.
"Would it embarrass you more to be controlled sexually by your daughter?" I asked. She nodded.
"But she doesn't do that. So your daughter is controlling everything non-sexual in your life. But what happened tonight?"
She looked at me, confused.
"Your other daughter controlled your sexual life, didn't she?" Cheryl looked up at me in surprise.
"You have one daughter controlling everything outside of the bedroom, and now you have another controlling everything inside." Cheryl glanced back at Karen, who wouldn't meet her gaze.
"Masturbate," I demanded.
"What?" she asked, looking at me again.
"Take that dildo lovingly provided by your daughter and start using it, while I tell you all about how things are going to change for you yet again," I instructed.
She picked it up and looked at me nervously as she started using it. I noticed that she had no trouble slipping it all the way in. When she pulled it out, it glistened. She started pumping with one hand while she played with her clit with the other.
"Where do you have that dildo?" I asked.
"In my cunt," she gasped.
"And where do you want me to fuck you?" I asked.
"Everywhere!" she replied.
"Where first?" I asked, re-qualifying the question.
"In my ass," she answered.
"From now on, it is not your cunt. It is not your pussy. It is not your ass. From now on, it is Karen's pussy, Karen's cunt, Karen's ass."
Cheryl moaned. "What do you mean?" she asked.
"If you want to use your cunt, you will need Karen's permission. She is responsible, and she has to care for it." I looked at Karen as I continued. "She has to make sure that it is pretty and shaven. She has to get it ready when I want it. If you want something in your ass, she'll lube you up. Your privates are now her responsibility."
I looked back at Cheryl. "I want to make it clear, she is not to do things specifically to excite you. She is not to make you cum. She is just to enable you to excite yourself, or me to excite you. When I decide to fuck you, she will lube you, she will grease up my cock, and she will position my cock at your hole. She is in charge of your sex. Do you understand?"
"Oh, God, yes!" she moaned.
"How does it make you feel?" I asked.
"Like the biggest slut in the world!" she moaned.
"Do you want to cum?" I asked.
"Oh, yes!" she cried.
"Then ask Karen for permission," I said.
She turned around, getting on her hands and knees, facing towards the door as she continued to pump the dildo in and out. "Please Karen, please can I cum?"
Karen looked at me in shock. She didn't know what to do.
"Do you not want this?" I asked her.
"I don't know!" she said.
"Well, she's not going to cum tonight unless you let her. Are you going to let her?"
She nodded.
"Then you'd better tell her that," I said.
"Cum, Mommy," she said, and Cheryl wailed as she obeyed the instructions.
It went on for about a minute before she collapsed, whispering, "Thank you, Baby."
I waited a few minutes for Cheryl to come back to us, then I told her to leave the room and get drinks for us. She walked out on wobbly legs, and I motioned for Karen to come in.
"Are you up to this?" I asked.
"I'm not sure," she said.
"Think about it," I told her. "If you are, then you can help your mother again tonight. If you are not, call me tonight and I will work out something else."
"If I don't do this, will I be able to see you and Mom?" she asked.
"Probably not," I said.
She nodded as Cheryl came back with drinks. After she gave Karen and me our drinks, she walked over and dropped down to kneel in front of me. "Please, may I ask you a favor, Jake?" she asked.
"Sure," I said.
"I know that you want the first hole that you use to be my ass, but would it be OK if I relieved you onto my body like we did last time?"
"You want me to jerk off onto you?" I asked.
"No, I want to jerk you off onto me," she said. "I've been very good, I think. Please can I have this?"
I looked over at Karen, and she had perked up.
"OK," I said. Cheryl jumped up and wrapped her arms around me, kissing me deeply.
"Thank you so much," she said, then dropped again and opened my pants, fishing out my hard cock. Karen moved over to get a better look as her mother started running her hands over my cock. She took her right hand and ran it between her legs, getting it wet. Then she surprised everyone when she started rubbing her juices on my cock and she reached over with her left hand and scooped up juices from between Karen's legs.
She started rubbing my cock with both hands, moaning for me to cum on her. Given the events of the day, you can imagine that I did not last very long, and soon I was covering her chest with my cum. As she milked the last drop, she said, "I'm not going to wash this off until tomorrow."
"As you wish," I said, with a smile.