Chapter Eighteen: Karen's Request
Karen came up to me at lunch the next day and asked, "When are you going to fuck my mother?"
I laughed, saying, "First it was, 'Are you fucking my mother?' Then it was 'Why aren't you fucking my mother?' Now it's 'When are you going to fuck my mother?' Your questions are getting progressively steamier. What's the next one going to be? 'Did you enjoy fucking my mother?'"
"If you do it tonight, maybe," she said.
I leaned back and looked at her for a minute. Then, with a smile, I asked, "Did you have a nice day yesterday?"
She blushed and said, "As a matter of fact, I did!"
"All of it?" I asked.
"I wouldn't change a thing," she said.
"Really?" That surprised me. I'd expected that there was some part of the day that she didn't enjoy. "Even the spanking?"
"Even the spanking," she affirmed.
"I want you to know that you didn't really deserve the spanking; normally I would not let Helen dictate that," I told her.
"Did you want me to be spanked?" she asked.
"Yes," I replied.
"Then I deserved it," she said simply. "Actually, I don't think that my next question will be 'Did you enjoy fucking my mother?'"
"What will it be?"
"When are you going to fuck me?" she said.
That threw me for a loop, because frankly, as stupid as it was, I hadn't thought about that. I should have. I should have realized that I couldn't do all these things and not fuck her. But I really hadn't thought about it. And now she wanted me to fuck her, and I'd bet anything that she was still a virgin. I had turned down Gemma for just that reason, and here was another girl asking me for that.
"I don't know the answer," I said.
"Well, I just want it on the table that my mother is obeying you, and you have promised to satisfy her. I believe that I am obeying you just as well, so I expect nothing less."
"You are obeying me as well as your mother?" I asked.
"I am following all the rules that you've given her that I know about," she informed me.
"Really?" I asked. "Which are those?"
"I don't have any hair below my neck. I don't wear panties at home. At home, I'm wearing the sexiest clothes that I have, and I've asked Mom to buy me more. I will obey anything that you say."
I shook my head. How had I not noticed that?
"You want the same things as your mother?" I asked.
"Isn't that what we've talked about since the beginning?" she asked. She sounded utterly and completely sure about herself. I had gotten into this really deep.
"So when are you going to fuck me?" she asked.
"I need to think about this," I said. "Taking your virginity is an important thing. I don't want to just do it like it was nothing."
"Well, you're taking my mother's virginity, even though it's anal," she said. "It shouldn't be too different."
"Let me think about this for a while," I said. "I'll come over to your house tonight, and we can talk about it."
"OK," she said. As she started walking away she turned to me and said, "By the way, it's not just at home that I don't wear any panties."
When I arrived at Karen's house that afternoon, I paid attention to what both women were wearing. Cheryl answered the door wearing a black pleated skirt that came to mid-thigh and a red button down blouse, tucked in tight and unbuttoned to her navel, clearly demonstrating that she wore no bra. She plastered her self to me, throwing her arms around my neck, and while she gave me a welcome kiss, I ran my hands up her bare thigh to cup her ass, confirming that she wore no panties either.
When I broke the kiss, I glanced over at Karen, waiting her turn. She was wearing a white miniskirt and a white tank top that was clearly designed to be worn under a cover-up, though it was equally clear that she was not wearing anything above or below it. Her magnificent tits were clearly on display. As her mother stepped away, she stepped forward, wrapping her arms around my neck and kissing me far more deeply than she would as simply a friend. It wasn't entirely intentional, but my hands slipped under her skirt just as they had for her mother, and she gasped into my mouth as she felt my hands squeezing the bare cheeks of her ass.
When I broke the kiss, which Karen ended only reluctantly, Cheryl asked, "Can I get you a drink or a snack, Jake?"
I accepted, and we went to the kitchen to get a soda. As Cheryl was pouring, I asked Karen, "Where did you get that outfit?"
"It's Helen's," she said defiantly.
"Did she give you permission to wear it?" I asked.
"No," she replied.
"So you wore it, despite knowing that you might get a spanking for it?" I asked.
"I had nothing appropriate to wear for you," she answered. "It's worth a spanking to be dressed correctly for you."
I shook my head. "We'll deal with that later. Cheryl, can we sit down and talk? You too, Karen."
We went to the living room, where they sat down on the couch, and I sat on a chair across from them. When I looked over at them, I could see right between Cheryl's spread legs, up her skirt to her shaved pussy. Cheryl saw me glance at Karen's closed legs, and she reached over to spread Karen's knees, affording me a view of her pink lips.
"Sorry," Karen muttered.
"You're encouraging her," I groaned to Cheryl.
"I shouldn't?" she asked.
"Why would you?" I asked.
"Karen is a sexy woman," she replied. "I want to make you happy, and I thought that seeing Karen would make you happy."
I sighed.
"Tell your mother the question you asked me today," I instructed Karen, trying not to be distracted by her puffy, glistening pussy.
"I asked you when you were going to fuck my mother," she replied.
"What did he answer?" Cheryl asked excitedly.
"He didn't," Karen replied, and Cheryl groaned in disappointment.
"Tell her the other question," I instructed.
"I asked when he was going to fuck me," she told her mother.
"Did he answer that?" her mother asked.
"He wouldn't answer that either," Karen said disappointedly.
"It doesn't bother you that Karen wants me to take her virginity?" I asked.
"Someone is going to," Cheryl said. "Why not you? I believe that you will do a good job of it, though you haven't given me an opportunity yet to be sure."
I sighed, realizing I was going to have to explain this. "Look, I'm going to tell you something, and it will have to stay between us. I was dating someone else, and things started to get hot and heavy. I realized that soon we would be fucking, and I would be taking her virginity. I also realized that I wasn't ready to settle down and commit just to her, and I didn't want to be the one that took her virginity and then just dumped her. I believe it is something that you should do with someone you plan to love for the foreseeable future."
I paused for a moment, realizing that it still hurt me a lot to think about.
"So that's why you broke up with Gemma, and why she was so pissed at you," Karen murmured. I just nodded.
"When did you lose your virginity?" Cheryl asked.
"A while ago," I said.
"And was it with someone that you planned to spend the rest of your life with?" she pressed.
"It's complicated," I demurred.
"Nevertheless, you seem to be placing an almost mystical meaning on the deflowering of a maiden," she said. "Yes, it is important to a girl. Yes, she will likely remember it the rest of her life. But that is also the case with her first kiss. The first time she gets felt up. The first day of college. Her prom night. The first time she prepared her mother to masturbate. There are lots and lots of memorable events, and this is just one of them. I think you are blowing it out of proportion."
I started to disagree, but Cheryl kept talking. "There is another thing though. Let's say you do take Karen's virginity, then what? Are you going to get rid of her? Are you going to stop seeing me? Let me ask you another question. Do you love me?"
I didn't know how to answer her last question.
"I accept that you probably don't love me as a girlfriend, as your one and only, but do you care for me? Do you want to take care of me? Do you care about my well-being? Do you want what is best for me?"
"Of course," I replied.
"Then you love me. Again, maybe not the way that you love a girlfriend, but more like you'd love a family member. And I'll tell you something; that love is often far more enduring than the flare of romantic love. Tell me if you love me."
I thought about it for a long time, while the women sat there in silence. I thought about what she said, really thought about it. When I knew the answer, the one she already knew, I said, "Yes, I do love you."
"And do you love Karen?" she asked.
I nodded. Karen smiled brightly.
"We both know that after you fuck us, you will have other women. I don't have a problem with that. I don't think Karen will either." She looked at Karen who shook her head.
Cheryl continued in a very low voice. "The life of a slave is much different than the life of a girlfriend."
Then she sat up straight and looked at me intently, and in a louder, more confident tone asked, "So when are you going to fuck me? When are you going to take my virginity?"
"You are a pushy little bitch, aren't you?" I asked with a smile.
"So punish me," she said, not giving an inch. "But answer my question."
I looked back at her and said, "My parents are going away this weekend. I will do it on Friday night."
Cheryl shuddered and squeezed her thighs together. She took a deep breath and asked, "When are you going to fuck my daughter?"
"Which one?" I teased.
"The one who's pussy you keep staring at!" she exclaimed. Karen spread her legs wider at that statement and looked at me expectantly.
"Saturday," I replied.
Karen squealed and reached over to hug her mother. I just shook my head, thinking about what I had gotten myself into. Then both of them launched themselves at me, nearly overturning the chair I was on. I had two squirming, big-breasted women pushing themselves at me, kissing my face and neck. My hands went around them, and seemingly on their own slipped under their skirts and a finger slipped up into each of them. Karen gasped in surprise and tensed, but Cheryl groaned deeply and seemed to melt into me. I gave them each a quick kiss and removed my hands from them. They sat back as I licked each of my fingers, comparing their tastes. They tasted much alike, though Karen was a bit sweeter.
"Friday," I said.
I got up to leave. On my way out I told Karen, "You may not remove that outfit until Helen has seen you in it. You will accept a spanking from either her or your mother, whatever she chooses. And you will receive it nude. After it is done, you will thank Helen for disciplining you because you behaved badly. Do you understand?"
Karen nodded while Cheryl smiled. I shook my head as I left.