Pranking Caleb

Author's note: I changed the way Kathy looks in this chapters image. I gave her a less realistic appearance and more of an anime/comic look. This allowed me to fix her breast size without making her look fat like my previous attempts. I also get a more consistent face and body over multiple images. My original Kathy AI image would give her wildly different bust sizes between each image creation because the realistic style interfered with the bust size selection. If the feedback is positive I will continue using this style for now. I do dislike how flawless her skin appears even though Caleb's cum is supposed to have that effect in the story.

Another issue I keep having is how much of her body that the AI will generate in each image. This image is supposed to be a 3/4 view but if I uncrop the picture it does funny things with her lower body. I am still learning that part of the AI.

In this chapter I list every single member of his family and harem that will have recurring appearances in the story, as well as a brief reminder of who exactly they are. I did this for those readers that would like an updated Character List. I am still working on that but I am unwilling to take too much time away from my writing to focus on it. I am working on it, but it remains a lower priority. If anyone is interested feel free to post your own spin off anywhere along the story that you wish. It will not hurt my feelings. Honestly, I would be flattered.

As usual I appreciate all comments and suggestions. Please comment here or over on my ko-fi account at https://ko-fi.com/samus1001

There is a question I pose my readers over there about the direction of a particular characters development if you would like to comment. Thank you, and I hope you enjoy the story.

Caleb’s group portrait was nearly finished, he was applying the last few touches and was quite pleased with how it had turned out. He had his watch to thank for that. Having the skills of a master painter was the only normality he had given himself that wasn’t a little sexual in nature or gave him some control over how others acted.

He stepped back to admire his work while listening to Kathy, Angie, and Marilyn laughing about something on the other side of the curtain.

Every woman in his family and harem was depicted on the large canvas. He even added Kathy’s harem into the mix. The painting was a bit crowded, but it wasn’t until he began adding Kathy’s girls that he realized how large the number of women that shared each others love had become.

The center of the painting was focused on Kathy in a tie dye bohemian sundress similar to the one she wore today. He had managed to get a picture of her that morning with his phone that he was using as a reference.

Beside her with their arms around each other stood Chris, Gabbie, and Angie. They were the core of his harem, and aside from his relatives, the four women he loved the deepest. On one side of them stood his mother June, his aunt Lori, his sister Hazel, and his mom and sister’s fiancée’s Amelia and Tina. At the end stood his grandmother Betty and his classmate Jamal’s grandmother Lottie.

Sitting in front of them were Angie’s mom Megumi, his hudog bodyguard April, his cousin Emily, his priestess Sonia, Kathy’s pets the hucow Amanda and hubunny Melissa, and at the end his pet hucat Heather beside Amelia’s pet hucat Lu.

On the other side of the painting stood Kathy’s mother Mary, Kathy’s sisters Cora and Brandy, his secretary Marilyn, his first concubine Coach Katie, the softball team captain Holly and finally Zack’s mom Donna. In front of them sat their principal Melanie, Angie’s pet hubunny Misty, Misty's fellow AV club members Michelle and Gemma, his pretend daughter Sierra, and on the very end Kathy’s pet hucow Amber.

He debated adding Heather’s sometime best friend Christie but Kathy hadn’t quite claimed her yet. He didn’t add the other two marshals Linda and Ramona either. Even without them it was a lot of women he was responsible for. He was responsible for the babies some of them carried as well. Eventually he would give all of the women babies, including Lottie and his grandmother Betty, even if he had to use the watch to make that possible.

The thought of pumping babies into all of them and watching them waddle around with big pregnancy bellies and milk heavy tits was making him hard. He closed his eyes as images of all the sex they had and would have in the future swirled around in his head.

His thoughts focused on Kathy and her beautiful eyes. He loved every part of her body, from her cute little feet to her gigantic tits, but her eyes he could get lost in. They were the reason he never got caught staring at her tits. As much as he loved her bouncy chest pillows, her pretty face and lovely eyes captured him every time he looked at her.

She was the ultimate boner inducer. In fact, he was rock hard even now. He loved the way she kissed him, and the playful way her tongue danced with his. He lost himself in a fantasy of them just kissing. She liked to kiss his neck and playfully nibble the skin before kissing down his chest.

His daydream felt so real and he didn’t want it to end. He imagined her kisses continuing down till he felt her breath on his crotch. He could practically feel her tongue as it licked the length of his cock before she left a kiss on his cockhead. The kisses and licks continued and sped up, almost as if there were two different mouths on him.

He loved the double blow jobs his girls gave him and he pictured one now. He never had such a vivid daydream in his life. He was fully clothed and his dick was at a weird angle, but in his daydream it didn’t matter. He didn’t picture Kathy and one of his other girls, rather he pictured two of her, licking and sucking him off.

He stumbled backwards running into the wall behind him as his daydream grew more intense. Suddenly there was a third Kathy in his mind. This one went to kiss him, their tongues battling in a friendly duel while he continued to receive the ultimate blowjob.

He was so lost in his daydream that he reached up to cup Kathy's boobs but his hands met empty air. She wasn’t there yet he could swear she was kissing him and sucking his dick at the same time.

In his mind the first Kathy took him all the way into her mouth and down her throat while the second one began licking and sucking on his balls. The third remained kissing him. Everything felt so real, so amazing, as if she really were triplets whose entire purpose was to bring him to climax. He put a hand over his mouth to stifle a moan, but that did nothing to stop the sensation of Kathy's lips and tongue from driving him wild.

He was on the verge of cumming in his pants when he heard giggling close by. Opening his eyes he saw Kathy, Angie, and Marilyn peeking around the curtain. Embarrassed but knowing they couldn’t read his mind he tried to stand up straight.

It was then that he realized the daydream hadn’t ended. He could still feel the blowjob and ball sucking going on in his pants. Kathy smirked at him right before he felt a tongue lick from his jaw up his cheek. Then he felt a pair of lips against his own, as the real Kathy puckered at him in a kissy face.

The shock when he figured out she was doing this to him with her magic caused him to lose control of his orgasm. He grunted as cum rocketed down his shaft and splattered against his pant leg as the girls laughed out loud.

He blushed even though his snake was still spurting. He looked over at them and saw tears in their eyes as they continued laughing at him. He couldn’t be mad though, that blowjob felt amazing. He briefly considered using the watch to make Kathy triplets for real, but discarded the idea as soon as it came to him. One of her was enough, three would kill him. He had both her real sisters anyway.

The three girls walked into the curtained off area. Angie was smirking like a loon while Marilyn was trying and failing to stop giggling. Kathy smiled up at him while playing with her hair. “You’re not mad are you? I thought it would be funny but I knew you’d enjoy it.”

He grabbed her by the tits and pulled her close. He then wrapped his arms around her and hugged her tight. After kissing her on the forehead he said, “Don't do that again Kat. That blowjob was too good. One of you is all I ever need. I'd much rather we explore our bodies together and share the experience for real."

Kathy lay her head on his chest and squeezed him back, crushing her tits against him. "I hope you don't mind if I use that spell on the others my love. It's a lot of fun."

Caleb tilted her head back and kissed her. He couldn't tell the difference between this kiss and the ones from her spell. When he pulled away he said, "I would be disappointed if you didn't. Between that spell and your shadow cocks one, the girls are in for a wild time. Just don't use it too often or everyone will forget about me."

Angie smacked him on the shoulder and said, "There's no chance of that doofus. Kathy's shadow spells are nice, but nothing beats the real thing."

Caleb shifted and it was then that he remembered the huge cummy mess in his pants when he felt it sliding down his leg. He pinched Kathy's ass making her yelp. "It's a good thing I have gym next period. You've ruined my pants babe."

It was at that moment that Bernadette, one of the cheerleaders, poked her head around the curtains saying, "Oooo, what's going on back here?" She grinned at Kathy and Caleb's embrace but then she saw the mess soaking through his pants and laughed before she called out, "Oh my goddess. Caleb got caught checking out Kathy's tits."

Another student pulled back the curtain to see and then more came over. Caleb blushed again as his classmates commented on the cause of his embarrassment.

"Ha! So Caleb is human after all."

"Yeah Caleb. Busted!"

"O.M.G. that's a big mess you got there Mr. Stretcher King. Was Kathy's boobies too much for you?"

"Wait? Kathy's magic punishes Caleb too? That's hilarious!"

"It's about damn time. I was starting to think Caleb was dead inside."

Caleb had no idea what they were talking about and he gave Kathy a quizzical look. She stood on her tiptoes to whisper in his ear, "I cast a rune on my boobies that causes any guy that stares at them lewdly to cum in their pants. They think that's what happened to you."

Caleb laughed and decided to play along. He loudly said to the room, "Okay, okay. So I took a peek. She's my girlfriend, heck we are engaged to be married. Can't a guy check out his girl once in a while? I mean, she's carrying my baby for crying out loud."

Angie was quick on the uptake and was known throughout the school for her funny pranks. She cackled, "Man, that took forever to finally get you. Do you have any idea how many guys have creamed their jeans just so we could play this little prank on you? It's at least a dozen. You must have the willpower of a statue if it took this long for you to peek at Kathy's tits."

Kathy smiled up at him and said, "Well it's about time you did. I was starting to think you didn't like my boobies."

Marilyn was slower to catch on. She had a puzzled look on her face when she said, "Wait, how does that spell work, because I've seen him looking. Heck, I've watched you breastfeed him."

Kathy thought quickly but a believable lie came to her easily. She made a mental note to explain everything to Marilyn later. "I doesn't work if all he does is glance at them. He has to stare for a bit and have naughty thoughts. Also I turn the spell off when I want him to look, and I never have it on at home. He can look all he likes or do anything else he wants to me there. But at school he is supposed to be providing his services to our teachers and classmates."

She turned to him and poked him in the chest while conveying her total devotion to him with her eyes. "You sir, are not supposed to be thinking about me like that when you are on duty. You were blessed to stretch and heal and breed as many women as you can. As punishment for your naughty thoughts I'm not going to clean you up and neither are the rest of the harem. You have to wear your shame till you get to gym class. Also, I'm sleeping with Chris tonight. You will be sleeping with Melissa until you've put a baby in her belly like you were supposed to do yesterday."

One of their classmates said just loud enough to be heard, "Wait, I thought Kathy belonged to Caleb. Can she boss him around like that?"

Kathy spoke loud and clearly, "I am his Harem Queen. It is my duty to see to it that my King puts his cock and cum inside as many women as I can. That is the duty of the entire harem and why he needs so many women to help him. We aren't just playthings for him to enjoy. He 'owns' us so that we may perform our duties without interference from any one else. By accepting his claim on us we are accepting the responsibility to aid him in his task in any way we can. We comfort him when the stress of his duties become too much for him. We encourage him, we guide him, and we do anything else he needs for us to do. We cook, we clean, we manage his finances, and we even read through the applications for his services. But above all, we love him. We give him all of our love so that he doesn't feel like an assembly line worker in a dead end job."

She paused to organize her thoughts before she continued speaking as if giving a speech. "So of course his mom and I have the authority to tell Caleb what to do, as long as it pertains to our own sworn duty. You all know how hard Caleb has been working. According to the Sisterhood, Caleb is the hardest working Stretcher King in decades, possibly centuries. But that means he is giving these women the cures or babies they need without feeling any love from them. He has to be with multiple women per day, every day. It's our job to see to it that he feels loved and doesn't get burned out and stop caring about his duty. We are in the unique position to ask him to slow down when we think he is working too hard, or push him when he isn't working hard enough. SO yes I can 'boss him around' but in the end, I do belong to him, and so does the rest of our harems. He can do whatever he likes with us, and have sex with us any time he likes, as long as he does his duty."

She turned back to Caleb and hugged him again. "You are doing an excellent job my love. But you gave Melissa your word, so you will breed her today. And you shouldn't be staring at my tits when other women are around that need your cock inside them, but I will modify the rune spell so that it doesn't affect you anymore."

She pretended to recast the rune but she didn't need to bother. The rune spell already contained that modification and was still full of mana. She already had to refill the rune several times today thanks to her choice of dress and lack of a bra. She felt surprisingly free but would not wear anything quite so revealing to school in the future. Punishing men for looking at her body was one thing, but this dress invited those looks, which felt a little like using bait.

The bell rang signaling the end of class, so the students made a made scramble to put their art supplies away. Three of their classmates uploaded the videos they had taken of Kathy's impromptu speech. Others posted the picture of Caleb and his cum stained jeans on their social media accounts along with captions on how they thought it got there.

Little did anyone outside of her closest friends and harem members know, but Kathy had an **** cuckquean fetish. It turned her on immensely that Caleb had sex with multiple different women each day. She figured the Kathy from before Caleb found the watch probably wouldn't think the way she did now, but it hardly mattered. This Kathy was devoted to Caleb with all her heart, and she would see to it that his bed was never empty.

Thank you for reading. Please leave a comment if there is something you would like to see. If you loved the story please consider buying me a cup of coffee at https://ko-fi.com/samus1001