Growing Up A Master - Cover

Growing Up A Master

Copyright© 2006 by MWTB

Chapter 13: A New Cheryl

BDSM Sex Story: Chapter 13: A New Cheryl - A coming of age story about a boy, from childhood until college, discovering his inner Master. Golden Clitoride Winner, 2006, Best BDSM Story

Caution: This BDSM Sex Story contains strong sexual content, including mt/ft   mt/Fa   ft/ft   Fa/ft   Teenagers   Consensual   Slavery   Incest   Mother   Son   BDSM   DomSub   MaleDom   Spanking   Light Bond   Humiliation   Harem   First   Oral Sex   Anal Sex   Masturbation   Sex Toys   Water Sports  

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.

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