Chapter Thirteen: A New Cheryl
The next time I was over at Helen's house, things were definitely different with Cheryl. The first thing that I noticed was that she had gotten a new hairstyle. Her blonde hair used to fall just below her shoulder blades. Now it was sculpted close to her head.
"Nice haircut," I told her.
"Thank you," she replied. "I'd hoped it would be to your satisfaction."
"My satisfaction?" I asked.
"Yes, that it met your requirements," she responded.
"What requirements?" I asked.
"You commanded that I have no hair below my neck," she said simply.
Wow. Cheryl was definitely taking things literally. I would have to be careful in my instructions.
"I'm pleased that you are following my instructions, but I meant no hair whose roots were below your neck," I told her. She looked stricken, so I said, "No, Cheryl, I don't blame you. I was not clear on my instructions, and you chose to interpret them in the strictest sense. I'm proud of you."
"Thank you," she said, her shoulders dropping and her body unclenching.
I looked her up and down, from her new pixie cut to her sneakers. She was wearing a bulky knit shirt and baggy pants.
"I don't mind how you dress anywhere else," I told her. "However when you are expecting me over, I want you to be wearing a skirt that shows me your sexy legs and a top that is tight enough for me to see your body underneath it. You are beautiful, and I want to enjoy that.”
"OK," she said.
I brushed her lips with mine before I went out to the back to join my friends, as Cheryl went off to her room. I was chatting with Ken when Cheryl came out with snacks. "Why did you change your clothes, Mom?" Karen asked.
I glanced up and Cheryl was wearing a tight, black tee shirt that, while not see through, did make it clear that she was not wearing a bra, with a black and white polka-dotted skirt that was halfway to her knees. On her feet were white sandals with three inch heels and straps that went halfway up her calves.
"I was warm in my other outfit," Cheryl told her daughter.
Karen looked over at me, but I just smiled knowingly at her.
Over the next few weeks I had many more exploratory conversations with Cheryl. I discovered that when she was 18, she had been dating a handsome college senior named Jim Harrison. He had gotten her pregnant and subsequently married her. Two years later she was pregnant again. They were together about ten years before Jim decided to trade her in for someone younger. Jim was well off and ensured that his first family was well taken care of.
"Were you this way with Jim?" I asked.
"Which way?"
"Deliciously submissive?" I responded.
A slight pink suffused her face while she shook her head. "It was different with Jim," she told me. "He was older, and definitely in control, but while I almost always did what he said, it was never a given that I would. I never stated my submissiveness, and he never overtly asserted his dominance. It was just a situation where he was naturally in charge."
"And how is that different from us?" I pressed.
She hemmed and hawed for a minute, then looked directly into my eyes and said, "With us, I've completely submitted to you, regardless of how inappropriate it is." She paused for minute, then asked, "Don't you like me?"
"I like you very much," I told her.
"Then why haven't you done anything with me?" she asked. "It's been over two weeks, and you know that I would do anything that you said, but you've only made me do little things. Don't you want to have sex with me?"
I looked into her eyes and I saw fear, self-doubt, even desperation.
"Because you haven't asked me," I told her.
"What?" she exclaimed in surprise.
"I haven't taken you because you have not asked me," I repeated.
She still looked confused, but her expression soon cleared. She stood up, then came over and knelt by my side. "Please Jake, will you please take me and make me yours?"
I smiled down at her and said, "See? Was that so hard?"
"Will you?" she asked.
"Yes, I will," I told her. An ecstatic expression crossed her face and she started to get up. I put my hand on her shoulder and said, "There are a number of conditions."
"Of course," she said. "What are they?"
"First, you will do what I say, when I say it."
"I already do that," she said confidently.
"Second, if you are to be submissive to me, you will be submissive only to me. If I see you being submissive to others, than I will assume you no longer want me to control you."
"Do you mean that I can't do what anyone else wants?" she asked with a puzzled expression.
"No, that's not it," I explained. "But what you may not do is obey someone when you know that doing so is not what you want to do. You may not let yourself be pushed around just to get the thrill of giving in."
She looked at me guiltily; she had clearly not realized that I was able to read into her motives so well.
"Third, no underwear around me."
She stood quickly and reached under her skirt, pulling down her thong and throwing it to the other side of the room, then dropping back to her knees.
"Fourth, I want you to continue dressing as you do outside of the house. Inside the house, however, I want to see a slut. I want your daughters and all their friends to wonder how this innocent mother became such a slut."
Cheryl blushed, but nodded.
"Finally, when we are around your daughters or others, you are to behave the way that we always have. While I'm sure that some will figure it out, we are not going to advertise our relationship.
"Do you understand these requirements?" I asked.
She nodded.
"Then ask me again," I demanded,
"Jake, will you please take me! Now!" she begged.
"Strip," I instructed.
She quickly stood and slipped her skirt off and whipped her top over her head. She had not been wearing anything else, except for the already discarded panties, so I saw her completely naked for only the second time.
I enjoyed the view for a few minutes before standing and taking her hand. I led her into the bedroom and sat down in the chair next to her bed. Cheryl stood in front of me. She kept moving her hands, as if unsure what to do with them. As I just watched her, she shifted her weight from leg to leg while a faint pink blush slowly moved down from her face to her chest.
"Do you masturbate?" I finally asked.
"What?" she exclaimed.
"Do you masturbate?" I repeated.
Her blush deepened and she nodded.
"Answer in complete sentences, please."
"Yes, Jake, I masturbate," she said.
"Manually, or with toys?"
"Both," she replied.
I looked at her with a raised eyebrow.
"I masturbate with both my hands and with toys, Jake," she corrected.
"Lay out all of your toys on the bed."
She avoided eye contact with me as she went to a drawer next to her bed and extracted a dildo and a bullet vibe.
"Is that it?" I asked.
She shook her head, and I said, "Answer in complete sentences."
"No, Jake, there is more." She went to her closet and pulled a box from her top shelf. Inside were two more vibrators/dildo combinations, another plain dildo and nipple clamps. I stood up and arranged all her toys on the bed. I noticed with pleasure that all the dildos were of medium size. A few were larger than me, but none appreciably so. I picked up the nipple clamps and looked at her.
"I have very sensitive nipples," she said.
"Just the kind I like," I replied.
I sat back down in the chair and said, "Masturbate for me."
"What?" she said. She said that word a lot.
"Masturbate for me, and stop making me repeat myself," I told her. "I want you to pretend that it is a regular night, and I want you to masturbate just like you always do. Ignore me."
She looked at me as if I were insane. Then she shook herself a little and started putting most of her toys back in the box. She put the box down next to the bed and took the dildo and the bullet that she had gotten from her drawer and put them by her pillow.
She laid down on her bed and closed her eyes. She started running her fingers around up and down her body, then started concentrating on delicately circling her nipples. The fingers of her left hand started moving between her nipples, squeezing and pinching them, while her right hand moved down over her flat stomach, her cute navel, down over her clean shaven pussy and gently over her lips.
She pulled her knees up out, completely exposing herself to me. I could see her little clit peeking out, and her pussy lips, puffy and red, just slightly opening. Beneath that, I could see the star of her asshole, opening and closing as she clenched her muscles. She dipped her finger slightly into herself, pulling out more moisture and rubbing it around her lips and clit.
She continued this for about three minutes, her breathing rate increasing, then, with her eyes still closed, she reached over and grabbed the dildo. She held it in one hand while opening herself with the other, as she slowly slipped it in. She moaned very quietly as she started gently pumping the dildo in and out. She released it with one hand, which went in search of her vibrator. She laid the bullet on her stomach as she fumbled with the controls. It buzzed to life in a pulsating pattern and she quickly grabbed the silver oval and pressed it to her clit. Her breathing increased yet again and she started moaning very quietly. She was pumping the dildo in and out while rubbing the vibrator over her clit when I started hearing her, almost sub-vocalizing, whispering, "Oh Jake, please fuck me Jake, fuck me so good!"
She sped up with her right hand, pushing the dildo in and out quickly while she pressed the vibe in her left hand harder into her clit. Then her whole body locked up and she spasmed, clenching every part of her body. Even as she was experiencing a spectacular orgasm, she was almost completely silent.
With a final jerk of her body, she finished cumming, and pulled the dildo out of her. She fumbled for the control to the vibrator, and when she found it the quiet buzzing ceased, leaving Cheryl's frantic panting as the only sound in the room, and even that slowly quieted.
Finally, Cheryl opened her eyes and looked at me with embarrassment. I smiled encouragingly and said, "You would not believe how hot that was."
She smiled shyly.
I stood up next to the bed and ran my hand down the side of her body. I moved my hand up, and she gasped as I ran my fingertips around her oversensitive nipples. My hand continued down her body and she writhed as I dipped a fingertip over her clit and into her hole. I brought my hand to my face and got the first taste of her. As I expected, she was delicious.
I ran my finger back over her pussy, then dipped it down to her asshole. She squirmed as I played around her nether opening.
"Have you ever had anal sex?" I asked.
"No!" she exclaimed sharply.
I ran my hands back up her body and said, "I thought that I told you to masturbate like you do every night, and ignore the fact that I was here. Why were you calling my name?"
She blushed and looked away, then in a quiet voice said, "That's how I've been doing it lately."
That admission made me smile. I stood there watching her for a minute, then said, "I notice that you are very quiet when you do yourself."
"Well, the walls are thin, and I don't want anyone to hear me," she said.
"But you have all this energy. I watch you, and it looks like your whole body will explode, but you hold it all in."
She just nodded.
"Do it again," I told her. "Do yourself again, but this time, I want you to let it all out. We are alone here, and I want to see you explode, not implode. I want you to shriek when you feel like it, scream at the top of your lungs."
"I'm not sure I can," she told me.
"I'm telling you that you will."
She nodded and picked the dildo up. She didn't close her eyes this time. She was looking into my eyes as she slowly inserted her toy into her already soaked pussy. She started rocking it back and forward, her rate of breathing increasing again.
"I can't hear you," I said.
Her shoulders slumped and she closed her eyes briefly, then she looked me in the eyes again and started breathing more heavily, moaning softly. I reached over and grabbed her vibrator, giving her nipple a lick as I was doing it. Cheryl gasped and moaned loudly. I handed her the bullet as I held the controls in my hand, examining it. It had five settings, so I started with the first.
Cheryl moaned again as the vibe started pulsating slowly against her clit. Her hand started moving it all around her clit. I flicked the switch to the next higher setting and it started pulsating faster.
"Yessss!" she hissed.
"What did you say?" I asked, moving the switch up one higher.
The pulsing sounded even harder as she screamed, "Yes! It feels so good!"
I flicked the switch all the way up to the highest setting, hearing the vibrator go to a steady hum. I dropped the controls and started removing my pants. Cheryl's eyes, which had been closed, opened wide.
"Are you going to fuck me now? Please, will you fuck me now?" she cried.
"No, not now," I told her. She moaned when my cock was exposed. I crawled onto the bed and put my dick next to her mouth. Her head practically leaped off the bed and her mouth engulfed my cock.
"Don't stop doing yourself," I said as I saw her lose concentration.
She started her hands moving again as her mouth stayed plastered on my cock, but after a few moments I pulled out.
"I don't want you gagged. I want to hear you cumming," I explained. I started stroking my cock as I watched her getting closer.
"Oh, yes, yes!" she moaned, the volume increasing. She reached up with her tongue and swiped at my cock. "I want your cock so bad! Why won't you give it to me! Please. Oh, I'm so close! I'm so close! I'm going to cum!"
"I want to see you cum, I want to hear you cum!" I demanded.
"I'm cumming!" she screamed as her back arched off of the bed, the dildo was pushed in as far as she could get it, and she shoved the bullet against her clit. As she shrieked in pleasure, my cock exploded, spurting all over her chest and face.
Her back was off the bed for over 30 seconds, until she collapsed, breathing heavily.
"How was that?" I asked.
"I'd rather be fucked," she gasped.
"But as an act of masturbation?" I asked smiling.
"Amazing," she answered.
I sat on the bed next to her and rubbed my cum into her skin. "I don't want you to wash this off until tomorrow morning," I told her.
"I won't," she said with a smile.
"I have a few other tasks for you."
"I'll do it," she said.
"You don't know what they are," I warned.
"I don't care."
"OK, first of all, I want you to go to a sex shop and get a couple of smaller dildos, a lot of lube and a small butt plug." She looked at me in shock.
"You have a virgin ass, and the first time that I fuck you will be in your ass," I told her. Her eyes widened.
"Are you going to obey me?" I asked.
She nodded. I was about to rebuke her when she said, "I am going to obey you and get more dildos and a butt plug so that you can fuck my virgin ass and take my last cherry, Jake."
I leaned over and kissed her.
"One more thing then, my obedient Cheri. I want you to use the dildos and work your way up so that your ass is used to having things in it. And I want you to masturbate every night. Not like you used to, but like you just did."
"But Jake, my daughters..." she began.
"Helen is already having sex, and Karen either is or knows all about it. I'm sure that both of them masturbate regularly, and I'm sure that they assume that you do; all you will be doing is confirming it to them. I want you to masturbate every night, and I want you to enjoy it. Will you do that, Cheri?"
She nodded. "I will, Jake. I will masturbate loudly each and every night."
"You don't have to scream so that they hear it; you just shouldn't hold yourself back."
"I understand," she said. "Jake, why are you calling me Cheri?"
"Cheryl is the sweet mother of two of my friends, and a friend of mine," I explained. "Cheri is a dirty little slut who will grant my every little whim." I ran my fingers through her sticky pussy, bringing them up to her lips to suck off. As she did, I said, "Right now, I am talking to Cheri."
She smiled around my fingers. I leaned over and kissed her deeply, getting a taste of her in the process.
"I'll see you later, Cheri." Then I pulled up my shorts and walked home.