Chapter Twenty-One: Karen's Big Night
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.
I started slamming her, as she moaned "Yes" over and over, until I finally pushed all the way in and held myself there. Her eyes opened wide as she stared at me. I pumped into her, over and over, and she hissed, "I feel you. I feel you cumming in me!"
I slammed my mouth on hers and kissed her hard. She wrapped her arms around my shoulders and pulled me into her. We stayed locked together for a few minutes, then I pulled back and asked, "Are you OK?"
"Wonderful," she said.
I smiled and I rolled off. We both lay panting on the bed. Cheryl embraced Karen and said, "You looked so beautiful! My little girl is a woman!"
"I was a woman before," she said. She looked at me and told Cheri, "Now I'm his woman."
We lay there for a minute, and Girl whispered something in Cheri's ear. "Really?" Cheri exclaimed.
Girl nodded, and Cheri leaned over and whispered to Karen. Karen didn't question whatever was said, she just nodded. Cheri helped Karen sit up. Karen rolled onto me and gave me a kiss. Then she moved down, and she and Cheri looked at each other over my cock. I glanced down as Cheri held up my limp cock, pink-tinged and covered in our juices. Then she licked up one side, and Karen licked up the other.
"You don't have to do that," I told them.
"Yes they do," Girl said.
"What do you mean?" I asked.
"Mistress Cheri offered her daughter's virginity to you. You accepted, and the result of that sacrifice is now on your cock. It is only right that they clean it off, and take it back into themselves."
Karen and Cheri kept passing my cock back and forth, licking and sucking it clean. Girl was going way overboard with this. I had intended to make it special for each of the ladies, but Girl was turning it into a major ritual. She was definitely pushing it farther than I had intended. I wasn't sure how to deal with that, or if I even should, as Cheri and Karen seemed content to follow her instructions.
By this time, my cock was quite clean, so I dragged both ladies up to me and snuggled with them, while Girl curled up at the bottom of the bed.
"Are you ladies OK with all of this?" I asked.
They looked at each other over my chest and both of them giggled. "Very," Cheri said, and Karen nodded her head. I looked down and saw two naked, busty, blonde-haired women. I was quite happy.
"When can you do it again?" Karen asked.
"You're not sore?" I asked.
"I'm a little sore, but that's not where I want it," she said.
"Where do you want it?" I asked.
"In my butt," she said, quietly.
"What?" I asked. I had not planned on that. "Karen, your mother has been preparing for that. She stretched herself out, so that it was not painful. You haven't done that. I hadn't planned on doing your ass today."
"But you have to," she cried. "It's not fair not to! I want you to have all of me."
"I can have it, but another time," I told her. She looked on the verge of crying.
"Sir, you really don't have to wait," Girl said. "Most women never have any preparation, and they still manage to do it. If you go slowly and be gentle, it can still be good for her."
"You've said quite enough today," I told Girl. "I don't want to hear another sound from you tonight!"
She nodded and bowed her head.
"Girl is right," Cheri said. "We've already prepared Karen. I'm sure she can take it."
"Et tu?" I asked. I looked at Karen and said, "It will hurt, more than I hurt Cheri, more than when I first took your virginity. Are you sure?"
"Yes. I want it! I want it this way. I don't want to prepare with anything. I want your cock to be the only thing in me!"
I shook my head and kissed her. "If it means that much to you, then I'll do it." Then I laughed. "I can't believe that I just reluctantly agreed to fuck a beautiful woman in her ass."
Karen and Cheri laughed at me as well.
"When can you do it?" Karen asked.
"Well the sooner we do it, the longer it will take for me to cum. You might not want that for the first time. Maybe we should get something to eat first, and then we'll see?"
"OK," Karen said, though she was clearly disappointed.
We went downstairs, where I had Girl make us some snacks. She did so in perfect silence. We ate without much conversation, though Karen and Cheri had big smiles on their faces, and every now and then they looked at each other and broke out in giggles. They sat on either side of me, and they couldn't seem to keep their hands off of me.
When we were done, I dragged Karen into the den, calling over my shoulder, "Girl, go get the lube and bring it here now!"
I heard Girl scamper away and Karen said, "Ooooh, goody!"
"We'll see if you still say that when my massive rod is pillaging your delicate ass," I said with a leer.
"Pillage away!" she said, and she dropped to her knees, pointing her ass to me, wiggling it seductively.
I knelt down behind her and bent over, burying my tongue in her pussy. She gasped and groaned.
"Wrong hole!" she moaned.
I leaned back and spanked her ass.
"Don't tell me how to use my woman!" I scolded.
"I'm sorry, Jake," she said contritely. "You can use me as you please."
I leaned in again and stroked my tongue over her puckered asshole. Karen hissed, "Yes!"
Girl returned with the lube, and I indicated that she should give it to Cheri, who was quietly playing with herself on the couch. Cheri came over and inserted the jelly into Karen's hole. I told her to use two fingers, and she did, causing Karen to groan even louder. Then Cheri bent over and sucked my cock into her mouth, working it over until I was rock hard. She poured lube on her palm and rubbed it all over my cock.
When I sat back, she guided me to Karen's ass. "Are you ready, darling?" she asked.
"Oh, god, Mom, I am so ready. Please, Jake, please take my ass!" She looked back over her shoulder, her sexy blue eyes pleading with me. I slowly pushed my hips forward, and she shrieked as the crown popped through her sphincter.
"Are you OK?" I asked.
"Just wait a minute, please!" she begged. She took a few deep breaths, then said, "OK, you can go on." I started pushing in, and soon I was completely buried in her.
"So big," she groaned.
"I can still stop," I said.
"You can't, not until you cum in me!" she said.
I started pulling back and forth, and I realized that despite having recently cum, I was not going to last very long. That was probably good for Karen, but I wanted her to feel good as well. I beckoned Girl over and whispered to her to get a toy. She ran to get it, and when she came back I pressed the bullet vibe that she gave me into Karen's clit. When Karen felt it, she clenched so hard that she nearly ripped my cock in half.
Cheri slipped herself under Karen's head, and began whispering to her how sexy she looked, how well she was doing, and describing how I was reacting to the feelings. Karen started panting and clenching, and I recognized it as her way of cumming. While Cheri had massive, mind-blowing orgasms, Karen came long and continuously. I started rocking harder and harder, pressing the vibe into her, and soon I was announcing my intentions.
"I'm going to cum in your ass," I told her. "I'm going to pour my cum into you. And when I do, I'm going to own it. I'm going to take your ass whenever I want, I'm going to take your pussy whenever I want. And you are going to give it to me, won't you?"
"Oh, yes, I will!" she responded. "I'll be yours! You won't ever even have to ask!"
I dropped the vibrator to grab her hips, and Girl was there to pick it up and press it into her. She also slipped a finger in as I started slamming myself into her, then I screamed as I unloaded into Karen. I held myself over her as I felt her shudder, and then I had to pull myself out. I collapsed as she remained on her hands and knees, cumming continuously as Girl kept the vibrator pressed on her. I watched her for another three minutes, until Karen begged Girl to stop.
Cheri kept stroking Karen's hair, telling her how good she had done, and Girl came over to put her lap under my head, so that I could rest as well.
"I swear, you ladies are going to kill me," I said.
"You'd better not die," Cheri said. "You've promised us much more."
I laughed.
A while later we went upstairs, and Karen and I had a lovely shower, washing each other off. She hissed when I cleaned off her pussy and ass, but she insisted that I do it. She cleaned my cock, then she tested to make sure that it was clean enough to eat off of.
We tumbled into bed, and I told Cheri that she was to enjoy Girl for the night, leaving Karen all to me. We nodded off in each other's arms.