Growing Up A Master - Cover

Growing Up A Master

Copyright© 2006 by MWTB

Chapter 21: Karen's Big Night

BDSM Sex Story: Chapter 21: Karen's Big Night - 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 women made me a hearty breakfast, with pancakes, bacon, eggs, fruit and more. Karen served me a huge plateful, telling me, "You need to build your energy up!"

I grabbed her as she started walking away and gave her a deep kiss. "Looking at you builds my energy up all by itself," I told her. She blushed and went to eat hers.

We spent the rest of the day lazing around and playing. We hung out by the pool quite a bit, and all the women took pains to make me realize that I was hanging with three very sexy women. At one point, Cheri pulled me aside and said, "I know that today is for Karen, but I need you to know that I want you so much. If she wasn't my daughter, I'd be doing everything to make you want to be with me instead."

I laughed and said, "Shouldn't it be the other way around? Shouldn't you be doing everything to make me want you, instead of letting me defile your daughter?"

"No," she said very seriously. "I am giving you my daughter. I am offering her to you."

I just looked at her, and then kissed her. "I can't wait to be with you again."

She smiled and just about skipped away.

I took a nap by the pool in the afternoon while the women prepared the dinner. I was having lovely dreams of frolicking naked women, when I was awakened by another blowjob. I looked down, and it was Karen's long blonde hair around my hips. She looked up and said, "We are going to prepare for dinner. It's time for you to get ready as well." She took another long lick of my cock, then stood up.

She helped me stand, then I pulled her into a kiss. We went into the house, and we each went to our rooms to prepare. I put on my suit and went downstairs. I sat at the table, waiting to see Karen in the outfit that I had picked for her. However, when she entered the room, led by Cheri, she was wearing the same dress that Cheri had worn yesterday. I must say, she looked lovely in it as well.

We sat down, and as the maids brought in our appetizers, I asked Karen, "Did you not like the dress that I picked out for you?"

"Oh, no, it was lovely," she said.

Cheri interrupted and said, "It was my fault, Jake. I asked her to wear this dress."

"Why?" I asked, confused.

She blushed and looked down. "I always wanted my daughters to wear my wedding dress at their wedding. I think of this dress in the same way."

"So we're married?" I asked jokingly.

She glared at me and said, "I never let my husband fuck my ass."

I was confused. I didn't understand what she meant, but when I asked her, she just shook her head and wouldn't tell me.

Other than that incident however, the rest of the dinner was much lighter than the last night's. Cheri had been nervous and worried. Karen was not. Karen was playful and eager. She laughed and joked with the maids. She flirted with me. She told Girl to hurry up and bring the food so that we could get to dessert. And soon, we were at dessert.

While I went to take my shower and change, Karen went for her preparations. I would say that the maids led Karen away, as they had Cheri the night before, but that wasn't the case. Karen was pulling at them, rushing them upstairs. As I went to shower and prepare, Karen went into the master bathroom and pulled her dress off and knelt by the tub before Cheri and Girl had even made it to the bathroom.

Girl instructed Cheri to start the bath while she started preparing the enema.

"But he's going to take her in the pussy," Cheri said.

"Not just the pussy, Mom!" Karen said. "He had you everywhere, of course he's going to do the same to me!"

Cheri shook her head, but made the bath. After the first application, Girl had Cheri do the second one by herself.

"You are going to want to do this to each other every morning," she told them.

"Every morning?" Cheri asked.

"Of course! What if your master is at school one day, and he sees some sexy cheerleader bent over, her ass peeking out of her skirt. All day he is thinking about sexy asses. Then, he stops by after school. You don't know which of you he'll see first, but when he does, he'll spin you around, lift your skirt and shove his cock deep into your ass. You want to be prepared for that!"

"That wouldn't really happen," Karen said, grunting around the feeling in her stomach as the fluid filled her.

"It has to me," Girl said.

Karen whipped her head around. "He did that to you?" she asked in surprise.

Girl nodded. "It was wonderful. Of course, not as nice as when he has been coming home from your house recently."

"You mean..." Cheri said.

"Yes, he'd get so worked up at your house that he would practically rape me as soon as he got home. He would use me as a masturbation toy while he thought of you."

"That must have been so wonderful," Cheri breathed.

They looked at each other, understanding how each was feeling, and then they kissed deeply, hugging each other tightly.

"Not to rain on your parade," Karen hissed, "but if you don't stop filling me I will explode!"

"Oh!" Cheri shrieked, and quickly turned off the flow and helped Karen to the toilet.

When they were done and in the tub, Karen asked, "Did it really make you feel good, knowing that he was thinking of someone else while fucking you?"

"Oh, yes, it made me feel special," Girl said.

"Why special?" Karen asked.

"I can explain, darling," Cheri said. "It is like the ultimate servitude. You are just a toy. You are serving someone so well that they feel that they can use you, without shame or embarrassment, just to get themselves off. It's... Maybe I can't describe it. You'll know it when you feel it."

"Have you felt it?" Karen asked.

"No, but I'm confident that I will soon," she replied happily.

Soon, they were ready, and the maids escorted Karen into me.


Whereas Cheri was willingly led into the room and to my bed, Karen behaved differently. As she was escorted into the room, she ran to me and wrapped her arms around my neck, giving me a scorching kiss. "Will you fuck me now? Will you fuck me, please, Jake? I'll be good for you, I promise."

She stepped back and pulled her clothes off. "Slow down, honey," Cheri said.

"I don't want to slow down," she complained. "I want to speed up. Please!"

I laid her down on the bed. Regardless of what she had asked of me, I was going to take my time and enjoy it with her. I kissed my way up her legs and she propped her head up so that she could see what I was doing. She moaned as my tongue first touched her pussy lips, and she shoved her hips up, trying to get more contact. I licked and kissed her sweet pussy, trying to savor it. I brought my fingers into play and felt her inside. I pushed in a little, and felt something I had never felt before, a barrier.

"You still have your hymen," I asked.

"Yes," she moaned.

"It's going to hurt when I fuck you," I said.

"I can't wait," she moaned. She was squeezing her nipples as I licked and fingered her. I played with her more, until she screamed in ecstasy and came. I moved up her body and took her hands off her breasts as I replaced them with my lips.

I moved up to her face and tried kissing her gently, though she practically attacked my mouth. I grabbed her hands and held them over her head. "Calm down," I told her.

She laid back onto the bed, panting, and I kissed her again, and this time she let me do it gently.

"Are you ready for this?" I asked.

"Oh, yes!" she moaned.

"Are you ready for me to take you?" I repeated.

"Please, yes!" she cried.

"Are you ready for me to take your cherry?" I asked.

"I need you to," she said.

I looked over at Cheri. "Cheryl, are you ready for me to take your daughter's virginity?" I asked.

"She is yours, just as I am," she said.

"You are giving her to me?" I asked.

"Yes, I am," she said.

I nodded to her, and she took my cock in her hand, took the opportunity to jack it a little, then placed it at the opening to Karen's cunt. Karen tried to push her hips up, but Girl held them down. Then Cheri pushed my ass hard, slamming me through Karen's cherry, burying me completely.

Karen screamed and I stopped moving. She was panting, looking at me wide-eyed. "Are you OK?" I asked. "Do you want me to stop?"

"No, no," she said. "It hurts, but I don't want you to stop. Please use me!" she said.

I pulled out a little, and she hissed, then I pushed back in. I was pumping her shallowly, but she was soon pushing her hips up to me. I began thrusting more deeply, pulling nearly all the way out with each stroke. She was panting heavily, and I was getting close.

"I'm going to come soon, Karen," I informed her. "Are you close?"

"I've... been... cumming... since... you... started," she panted.

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