Caleb Woke Up Ch. 07

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Continuing harem fantasy of a naive eighteen year old boy who finds a magic necklace and his interactions with women who start throwing themselves at him, even his mom and sis.

Sci-fi, mind control themes.

*** Good Morning – Day 2 ***

Caleb woke up to sunlight gently streaming through the windows, and sunlit dust particles floating through the air. It was magical.

He noticed that it was a few minutes before seven. He stretched out in his bed and yawned, reveling in the afterglow of last night’s scrumptious sex dream. He had never dreamt anything that wild or vivid before. His previous dreams had only allowed boob touching over the clothes. Dreaming about sexual encounters with a buxom pixie, the pastor’s wife, that youth director/goddess, and his mom was light years beyond anything he could have ever imagined. The unconscious mind is a wonderful thing. I should feel guilty about this, but maybe the guilt can wait until later. I’m too tired for guilt. Let’s just enjoy the moment, he thought groggily.

He reached down to his crotch expecting to feel the dried crusty discharge on his pajama bottoms from what must have been a huge wet dream, but was surprised to feel that there was no crustiness and no pajamas, just a bare naked morning woody.

What the hey?

He noticed a towel on his pillow, the one from his dream, and suddenly sat up in bed as his mind started racing, Am I still dreaming? Oh God, did I have sex with Mom? No, it can’t be possible. He reached up to feel the necklace, and, sure enough, it was there. Holy crap, Dad’s going to kill me!

He looked around the room, and all traces of last night seemed to be gone. His mom, as well as her garments, were absent, and his dad wasn’t actively stringing him up by his toes. Did I just forget my pajamas last night? But I remember putting them on, right?

Before he could settle things in his head, the bedroom door flew open, and his sister Anna came bounding in wearing her honey blonde hair in pig tails and sporting her thick framed black nerd glasses she usually reserved for studying. Caleb gawked at her in astonishment, as he propped himself up on his elbows. Her long dancer legs and ample cleavage were on display due to her thigh length, white men’s V-neck T shirt. This was quite an aberration from her usual flannel night gowns and ankle length robe.

“Good morning, squirt. Did you sleep well last night?” she grinned.

“Uh, hi Anna. I guess.”

“Did you have a good time with Gretchen? I didn’t hear you come in?” Anna asked, as she closed the door behind her. She bent down to look under the bed and sneaked a peek in the closet.

“Looking for something?”

“Just wondering if you snuck in a girl?” she said as she looked over at him and grinned.

Caleb nervously commented, “No, no girls here.” I think! “Did you need something?”

“Mom thought you might need some help getting out of bed.”

Caleb started squirming and wondered, How much would Mom tell her? Geez, was there anything to tell? Maybe I’m just having crazy delusions.

Anna continued teasing, “Why would Mom think you might be tired this morning? Were you up late last night? Did you get lucky with Gretchen or something?”

At least she didn’t reference Mom. That would be too weird to talk about. Must protect Gretchen though. “Uh, well, I did drive her home, and we talked for a little while,” Caleb offered.

“Talked huh. Is that all you did? Did see teach you how to kiss yet?”

He was a terrible liar so he decided to come clean with a partial truth, especially since Gretchen had already confessed as much to Anna. “Um, maybe a little. But you can’t tell anyone! She could get in trouble.”

“Well, I wouldn’t want to get her in trouble, but maybe I need a little something to ensure my silence, you know what I mean?”

“Wait, what? You want money?”

“I was thinking something more personal. How about if we continue from where we left off in the church parking lot yesterday. It’s not nice to leave a girl hanging.”

“I can’t do that.”

“Why not?”

“Well, you’re my sister.”

“But doesn’t it make it a little more exciting just because I’m your sister?”

While she was talking, she reached down and grabbed the bottom of her T-shirt with both hands, and slowly lifted her T-shirt, exposing her white cotton panties. Caleb’s eyes locked onto the teddy bear on the front. Then she raised it further, revealing her flat stomach. Her belly button seemed to wink at him as she did a little shimmy.

“Like what you see?” she asked.

Caleb could only raise his eyebrows, not sure how to respond, but there were plenty of subtle and blatant hints that for her to glean that she was getting to him. As his body started humming and his heart started pounding, he turned beet red, started breathing hard, and his make shift pup tent beneath the sheet wiggled. Yes, she could tell that her victim was in terrible discomfort.

Anna loved the role of the cock teasing seductress. It was becoming addictive. Her panties were soaked, but then she had been in a continuous state of arousal since şişli escort last night’s dinner. It was driving her batty. She had tossed and turned as wild fantasies played out in her head. She had woken up to soaked underwear and sheets. Her body was craving release, so her goal this morning went well beyond teasing.

“Doesn’t it feel deliciously naughty, watching your innocent sister strip off her clothes?” she asked as the shirt continued its slow rise up over her cantaloupes which revealed a pink satiny bra.

This is like a replay from the church parking lot, only more so, Caleb thought.

She pulled the white T-shirt over her head and held out her arms. “Well, what do you think?”

Caleb looked at her sister with amazement and guilt filled desire. She was now standing there with her white cotton teddy bear underwear, her large mounds slung up in a pink bra, hair in pig tails, and wearing her black nerd glasses. His mouth went dry, his tongue felt thick, his throat tightened up.

He responded with, “Bazizwrfmzly.”

She smiled at her tongue-tied little brother, and climbed up onto the bed straddling his waist as he fell back, helpless to resist. She pressed her crotch down and rubbed it against his morning wood only separated by his sheet and her panties. Caleb groaned from the pelvic pressure on his prick.

“Caleb, do you want some help with your problem?”

“Ungh. What problem?” He was having trouble thinking as she slowly rubbed herself on his crotch.

“This problem down here,” as she looked down at his erection poking up against her from beneath the sheet.

“Anna Banana, what are you doing to me?” he groaned as she continued to dry hump him.

Anna was thinking, I feel so wicked, but it feels so good to tease him this way. He’s just so adorable and innocent. Who could resist him? And I really need him. This feels nice, but I think it’s time for phase two.

She scooted down his legs, and started tugging the sheet down his body.

He tugged back. He didn’t want her to see him naked.

“Feeling a little shy? Do you need a little persuading?” she questioned. “Tell me, have you have ever wanted to see my boobs in all their glory? Like, no bra, swinging in the wind.” She paused for effect. “This could be your big chance.”

She reached behind, and unsnapped her bra. She stopped to watch the anticipation in his eyes. “What if Mom were to walk in right now, what do you think she would say?” She saw his stiff bump waggle.

She slid the bra off her shoulders and arms, and flicked it onto his face, obstructing his view from her now exposed milk jugs. She giggled at his predicament.

While caressing her round, full breasts she asked, “So what do you think, Caleb? How do these compare to Gretchen’s?”

He let go of the sheet to pull the bra off of his face. A choir of angels sang triumphantly in three part harmony in his head, AAAHHHH. It was like a great revelation. They were blindingly beautiful. He was stupefied.

His sister, as planned, took the opportunity to reach down and yank the sheet off of him.

“Hey, no fair!” he exclaimed, as he quickly covered his raging hard on with the bra in his hands.

“I think it’s fair. You know, ‘tit for tat’,” she giggled.

Caleb never understood that saying, and then it dawned on him and he smiled. “Oh, is this what a ‘tat’ is?” he asked while he motioned with his eyes towards his bra covered erection. “I always wondered about that saying.”

She thought, He’s a dork, but at least he is a cute dork. “Wow, nice one bro,” she smiled. “You know, you really do have a nice ‘tat’. Remember when I saw it yesterday? Under the table at church?”

What she said didn’t register. He was too busy soaking in the vision of this bare chested, bodacious, buxom blonde in her teddy bear panties. His face went slack. He started to drool.

Anna laid down on the bed next to him, with her breasts leaning up against his arm and spilling onto his chest. She ran her fingers along up and down his smooth torso. He felt extremely exposed, but his hands and the bra were still covering his crotch. He watched her nervously.

Anna changed her tone and started talking gently, almost whispering. “You know Caleb, Mom just sent Dad out to get some milk so we have a little time to help you out with your affliction.”

“My affliction? What do you mean?”

“I woke up early this morning, and Mom was already up. We talked and she told me how you were burdened with these nasty erections, and we might need to help you out once in a while. Holy cow, I couldn’t believe it when she told me, but I was happy about it. I don’t really care why we’re doing it. I just can’t believe I got permission to do this. “

She reached up and gently grabbed his chin, looked him in the eyes, and gave him a disarmingly soft kiss on the lips that caused some of the tension to ease out of him.

His breath quickened at the idea of taking the next step with Anna. He thought, Is it the right thing to do? Of course not. His conscience was battling the logic of his other head, which simply countered with, Look at her. She is mecdiyeköy escort so hot , and it will feel so good!

“And so Mom thought that maybe we should take the edge off before going into church.”

She gave him another soft kiss, and let her hand trail back down his chest to his stomach.

“So did you understand that? Mom gave us permission. A good boy does what his mom wants, right?”

She gave him another kiss, and her hand trailed down from his stomach to his crotch. This time he kissed back a bit, and gave no resistance as she pulled his hands out of the way of her goal. She put her hand on her bra that was still covering him up.

“And we really wouldn’t want this thing going off during Pastor Anderson’s sermon, now would we? Can you imagine a whole congregation of pious women all achieving orgasm simultaneously because of you?” she whispered while wrapping the bra around his prick, and gently rolling it around. “Although I bet the offering plates would be overflowing if you did. Can you imagine?”

She started kissing him slow and passionate as she slid her soft bra around and up and down on his dick. He moaned. The satin felt really good. She went up on one arm so her head was above his so she could get better leverage on the pumping and the kissing, and it caused her breasts to trail over his chest as they rolled in waves from the movement of her arm.

And that scene continued peacefully like that for a minute or two while she stroked him with his bra, whispered loving and sexy things into his ear, and frequently kissed him. “You’re such a wonderful little brother. I am so lucky to have you. And you’re so handsome and nice and funny. And your wonderful cock. It’s so beautiful. It’s going to drive the girls wild. You’re going to make some girl really happy. I’m a little jealous. I wish I could be your girlfriend. I want you in me. I want your cock, your wonderful cock.”

He imagined himself penetrating into her, filling her up with his semen. “Ooh Anna, I think I’m going to …” And his face turned red, he held his breath, and he spurted a geyser that shot a foot in the air landing on her hand and bra.

The orgasmic wave washed over Anna as she was pumping, and she collapsed on top of Caleb as she started convulsing and mashing her tits into his chest, with her head next to his, face buried in the pillow, and a pig tail lying across his face.

“Oh gawd, that’s so good,” she said softly, as she started to recover and rose up on one arm to look at him while catching her breath. “You’re amazing. I wonder if Mom could feel that too. Wow, that was hot, wasn’t it?”

He was still panting while staring at the ceiling. He didn’t respond, but he thought, My sister wants to be my girlfriend? She wants to have sex with me? The fact that he might have given his mother another orgasm just made him smile. He loved that woman. It’s weird how he had so much resistance to his sister, but just melted and folded for his mom. Maybe it’s the approach. She comes on a little strong. It’s a little intimidating.

Then she grinned and said softly, “Mom also told me I should eat some of your sperm so I could get some protein.”

That jarred him from his thoughts. “What? She did not say that,” Caleb responded, calling her bluff.

“Well, maybe not in so many words, but she did say I should get some protein. She might have meant yogurt,” she winked.

His sister proceeded to lick up what she could off her hands and her bra.

“It tastes so good, just as good as yesterday. You should bottle this stuff,” she commented.

“Yesterday?” Caleb asked. “I don’t remember that!”

Her face reddened. “When you blacked out. You looked so afflicted, and I couldn’t help myself.”

“You’ve already done this?”

“That was my first time. You’ll need to teach me more about what makes you feel good next time.”

Next time?

Then she started going after the wads on and around his privates. He wasn’t fully erect, but as she continued her nutritious preening, she was rewarded with his hardened member.

Then she stopped and got this serious look on her face. She looked down along his torso at his face and stated, “Caleb, I want you to take my cherry.” Then she continued to lick. She was just finishing up.

“What? You mean … I can’t do that. You’re my sister.”

“Yeah, I think we already established that.” She got a serious look as she sat up on his bed, and straddled him again with just her soggy panties between them. “Caleb, look at me. I need this. I’m begging you. I know this is wrong, but I really need this. I’ll do anything you want, any time you want. Just be my first, OK?”

“Can I at least think about it?” he asked.

“Well, I kinda need it now. I don’t want to wait.” She needed to persuade him. She had a desperate look in her eye like an addict who needed a fix. She pulled her wet panties to the side, and started sliding her slick slit across his gilded rod.

“Oh Anna. What are you doing?.”

“Just relax bro. Let me do all the work. Doesn’t that feel good? Imagine what it would feel like inside.” She sped up a bit. She was getting a little frantic.

Oh man, she’s not making this easy.

“Caleb, I need this. Please, don’t reject me.” She stopped sliding to reach down and bring his hands to her bare chest, and then resumed her sliding. “Play with my tits. It’s OK. I want you.”

His eyes were closed and he was groaning as his head rolled from side to side because what she was doing and asking both felt so good and so wrong. “Oh Anna. This is so bad.” But his hands started groping her chest.

“I prefer to think of it as naughty,” she explained, like she seriously thought that would make a difference.

He was slipping. “Oh Gosh Anna, I don’t know. It’s not that I don’t want to, I really do.” He opened his eyes to behold the glory of his naked sister. “You’re so gorgeous.”

“Just say ‘yes’ Caleb. Don’t you want to fuck your big sister? Don’t you want me?”

He started getting a little frustrated. His senses were overloading. All reason went out the window as his lusty penis took over.

“Anna Banana!” and he reached down to her hips and held them. “Stop!”

She registered shock as she halted. Is he going to turn me down? She was terrified.

“Now, put it in.”

All at once she was jubilant and relieved and guilty and nervous. She bent over and squished her chest to his, and give him another passionate kiss out of gratitude. She started crying, and her tears started dripping onto his cheeks which caught Caleb off guard.

“Anna, what’s wrong? Are you sure you want this?”

“I know it’s confusing Caleb, but this is really important for me. I’m sorry I’m practically raping you, but I can’t help myself. I’m so hungry for this. Don’t hate me OK?” she sobbed.

“I could never hate you. You’re my ‘Anna Banana’. You’ll always be, no matter what.”

Her guilt assuaged mildly, she gave him another passionate kiss, and she reached down and started guiding his dick into her pussy.

“Oh God Caleb!” Her eyes went wide as an electrical bolt shot from her clit and out to all extremities. After a second she regained her senses, and started to grind and slowly coax it in.

“You all right?” He asked.

“Caleb, yes. It feels wonderful, but it’s so big. Will it fit? I’ve been using um, ya know, tampons, for like years, but this is so much bigger,” she groaned.

It slid in an inch with some effort. She was well lubricated, but it was just tight.

Caleb looked on in awe. This is really happening.

“It’s starting to go in. Oh God, ooommng,” she mumbled until progress stopped. Then she stated, “Fuck! I can do this.”

She pulled up a fraction, and then tried pushing down harder. She made a little more progress, and she slid down stopping half way to accommodate his size and steady herself. She gazed down at Caleb through her black nerd glasses with a look of steely determination.

“Fuck, I can do this. Fuck, I can do this,” she repeated several times. She was convincing herself. She was tenacious.

Caleb chuckled and said, “Yes, you can do this. You’re like the little engine that could.”

She ignored the joke. She was focused. She raised herself up a couple of inches, and slammed herself down right to the hilt of his sword. “Ungh,” she moaned. Her breasts were shaking and wobbling from her thrust.

Her eyes were still teary as she smiled and exclaimed, “Fuck! I knew I could do it.” She had never been happier.

Tears of joy streamed down her face as she slowly claimed her prize by slowly riding and grinding on her brother. Her glasses started to slip down her nose. He reached up and took the glasses off and placed them on the night stand, and gently wiped her tears as she rode him.

“Oh thank you so much Caleb. Oh man. Oh God. Marry me. I want your children. Oh God. Is it good for you? “

“Ungh. You feel amazing, and Ungh. You’re so happy.” It’s really weird, but somehow I’m glad I could do this for her, but it feels like more of a favor.

She paused to give him another passionate kiss. She leaned over him with her outstretched arms and grinded on him, and slid herself back up and down as her pace increased. Those years of dancing were paying off. She was moving in all the right ways.

“Oooh Good Gravy!” he exclaimed. He was really enjoying this.

Caleb reached over and felt her ass for the first time. In for a pinch, in for a pound I always say. Since he was already penis deep, he decided he wanted to know every inch of this woman. He reached under the panties through the leg holes, and back to around her crack. So smooth and fleshy. His hands continued to roam around her lower back and up then around to her chest. He remembered how some of the other women had liked that. He started with caresses, and progressed to pinching and groping. She moaned. She seemed to like that. He came back down to rub his hands across her thighs. He reached down between them and felt the front of her panties, and pulled them further to the side and felt her hair patch. She was longer and curlier than Gretchen, but it was a fine soft hair. On a whim he scissored the bottom of his cock with two fingers on each side just as she was on an up stroke. His hand was turned up, and he reached up to cup her as she continued to bounce on him. The top edge of his palm caught just where her clitoris resided.

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