The Herd's First Milking

Lori tried to get her laughter under control. She had dragged Caleb back to his bedroom as soon as he and Helena came inside and the news spread around the mansion. "Oh, Oh it hurts. I... HA! Oh my sides... You... You knocked up the Mother Superior. Oh god... I can't... I can't stop laughing..."

"Aunt Lori, It's not funny!... Well okay, it's a little funny. But think about it. This means I could get Lottie pregnant, or Grandma."

Fresh laughter burst from Lori's lips. "Oh! Oh Caleb!... You... Could knock up my mom!.. Oh god... You have to... Breed her good!.. Make her a mommy again... Give me a new baby sister... Hehehe..."

Caleb waited for Lori to get ahold of herself, which took some time. She lay on his bed occasionally giggling like an idiot. When she finally stopped, she sat up and looked over at him. "Okay huhu. I think I'm done. Oh man. I haven't laughed like that since the time June found Dad's condoms when we were young teenagers. Your mom thought they were balloons. She blew them up and was playing with them when Mom and I got back from the store."

Sudden realization hit her and Lori blurted, "Come to think of it, that's around the time Mom and Dad started fighting all the time. Holy shit! I just realized that was when Mom found out about Dad's cheating."

Caleb laughed this time. "I can't imagine my mother not knowing what a condom is. She bought me my first box. I only got to use a couple though. I found the watch-"

*Knock Knock*

Caleb cut himself off and turned to the door as it swung open. Misty stood on the other side in a string bikini that looked very good on the chubby large breasted hubunny. "Excuse me Caleb. We were going to go out and use the pool, but Amanda's herd are here for their milking session, and Amanda said to come get you."

As Caleb got off of the bed, Lori remarked, "I get why Kathy loves hubunnies. Carrots is fucking hot in a bikini."

Caleb grinned as Misty blushed, the inside of her long ears turning a bright pink.

Caleb looked Misty up and down and said, "Yeah. I totally agree. Every time I look at her I get hungry for carrot cake."

When Caleb walked into the bedroom that the milking tables had been set up in, he was in for a surprise. His mom's friend Roberta was chaining a nude young hucow to one table while Amanda was chaining another nude hucow to the second table. He couldn't see the faces of the two new women but he recognized Roberta.

His mother had told him what to expect, but he had never seen her in her hucow form until now. She was a bit taller, and the black splotches were not much different from Amanda and Amber. The main difference from the Roberta he remembered was her tits. She'd been large breasted in her human form, bigger than his mother, but now she had milk tanks to rival Brandy. She wasn't super busty like Chloe, Mary, Kathy, or Amber's gigantic knockers, but she still had an impressive set.

Amanda was the first to spot him. She stopped working and said, "Caleb, let me introduce you to our newest herd member. This is Lily. She's a Scottish breed, hence the brown spots. You already know Roberta and Connie."

Lily still had her arms and neck free and she smiled and waved from her position kneeling on the table. Caleb wasn't surprised to find her good looking. He knew Amanda wanted pretty hucows for her herd.

Roberta smiled brightly at him as well. He smiled back and waved to the two hucows. He took a moment to greet Amber as well. She was seated in a recliner reading the owners manual for the new tables while one of the harem breast pumps worked her newly enlarged tits.

This was his first time seeing her in an upright position since he bred and cum covered her. Her tits were even bigger than before, but they were not nearly as perky as Caleb had hoped they would become. While much improved, they still had significant sag to them and rested on her lap, almost too large for her to reach her nipples now. It occurred to him that that might be a good thing. On the nights that Amber slept with him he could share one of her tits with Kathy as a pillow and still be able to cuddle his girlfriend.

He turned to Roberta and the young hucow on the other table. "I know Roberta, but I haven't met Connie before... wait! Connie! That's your daughter?"

Connie hadn't looked up at him and he noticed the white skin along her flanks turn bright red. Connie had come over with her mom many times when they were younger. He remembered having a bit of a crush on her when he first discovered what sex was. Unfortunately Connie grew up, got married and stopped coming over when her mom visited. He continued to Roberta, "I guess I should have known she was a hucow if you are."

He then spoke to the blushing young woman that was still hiding her face, "Connie, don't be embarrassed. You have nothing to be embarrassed about, but if you want me to leave, I will."

"No, you will not. Connie will have to get used to you milking and mounting her. She needs you to breed her too. Her husband doesn't have a stretcher. You are their bull, and she can get over her embarrassment, or leave the herd," June said as she walked into the room. Mary followed her in.

Both women were in bikini's and Caleb felt his cock begin to harden at the sight of the two mothers where the two naked hucows hadn't. In Caleb's opinion, a woman that was barely covered was more of a turn on than a completely nude one.

June moved to assist Roberta while Mary joined Amanda. Mary looked up at him with a smirk and said, "You might as well get naked sweetie. You can mount Lily first. Lily would you like a breeding or just the orgasms?"

Lily had her head laying upon the table cushion and she didn't even look up as she said, "Breeding please."

Mary chained down her right arm and said, "Have you got a breeding ring in?"

Amber spoke up and said, "She won't need it. Caleb has had enough hucow milk he is strong enough to endure. I couldn't clamp down on him at all when he bred me earlier, and I exercise my pelvic floor muscles every morning."

Mary smiled and shook her head, "I forgot what hucow milk does to Stretcher Kings. Ok Caleb, she's almost ready. We just need to put the milkers on and you're good to go."

Amanda walked around to Lily's rear and said, "Not yet Mary. I've got a lot more to hook up if she wants it. Lily, these tables have a clit vibrator attachment. Would you like us to slide it in place? We have a couple styles on order, but it came with a rabbit vibe."

Caleb could hear the anticipation in Lily's voice, "Yes please. I want the full experience. I've never been on a table this fancy before."

After reaching between Lily's legs, Amanda walked over to a shelf near the wall and said, "Help me with these Mary. They are the massagers. If she wants the full experience, we will give it to her."

As he got undressed, Caleb could smell the room filling with the scent of horny hucows. When Amanda and Mary stepped to the side of the machine, Caleb saw how little of Lily's body remained uncovered and joked in his best Obi Wan Kenobi voice, "She's more machine now than woman."

He heard Lily's muffled, "Twisted and evil." He laughed and stepped behind her. Her ass was prominently displayed though her back and thighs were covered by the massagers. He stepped on the pedal that spread her legs and watched as her dew dripped onto the floor.

He looked up and nodded to Amanda. She started the machine as he began rubbing his cockhead along Lily's slit. She yipped and called out unintelligibly as the massagers, milkers, and vibrator started up, but he wasn't fully hard. This setup with Lily almost completely covered up was hardly boner inducing.

She had a nice ass, but he felt like he was about to have sex with some sort of sex doll while everyone watched. He figured Lily would be as tight as the other hucows he had fucked, so he would need to be an iron bar to get inside her. He looked over at Mary for inspiration. The sight of her bikini clad tits were helping, but he wanted more. "Mary could you come here please?"

When she came around the table she saw the problem immediately. He wasn't completely flaccid, but if he tried to fuck Lily right now it would be like pushing a thick rope. She reached for his cock and began stroking as she used her other hand to pull him into her cleavage. She closed her eyes and enjoyed her lover motorboating her tits while she said, "Amanda, we forgot the breeding lube."

Amanda leaped to her feet while muttering, "Shit. I knew I was forgetting something."

Caleb reached up and lifted the bikini top off Mary's massive jugs. He hefted them and smushed them against his face. He felt the cold lube being applied to his shaft and his cock stiffen from the combination of handjob, lube, and tits. He said to no one in particular, "Put me in her." He was too busy enjoying Mary's tits to do it himself.

A hand on his ass and a tug on his dick moved him into position. He could feel the heat of Lily's pussy as his tip pressed against her honey hole. He took a step forward and began the long slide into her snatch. She let out a moan that turned into a moo as he began to stretch her insides.

This was his favorite part of fucking a new woman. That first stretching as her internal organs shifted and her love tunnel elongated to accommodate his big dick. The moans and whimpers as her slit was stretched further than it had ever been. He reveled in the feel of her tight velvety snatch.

He pulled his head away from Mary’s tits so that he could step closer to Lily and get his cock in deeper. Her pussy was exquisitely tight and slick with her juices. He might not have needed the breeding lube, but he enjoyed the super slickness it gave his cock. Suddenly he felt the clit vibrator on his balls as he finally sunk all the way in.

Lily gave out a happy sigh and then half moaned, half mooed as he began thrusting. Mary moved around behind him and began giving him a massage that quickly turned into her nibbling his neck while just running her hands over his body and her tits against his back.

Mary whispered next to his ear, "You're such a stub Caleb. I love how you look when you're fucking a fresh pussy. I know why my daughter brings you so many new women to breed. You look so fucking hot I want to beg you to do me next. But I can't, can I? There is another fresh unstretched pussy laying over there. She needs your cock more than Lily does. Her husband's dick is tiny. He can barely get it inside her, not nice and deep like you can. She needs a long thick dick to put a baby in her belly. Your baby. Now pound this pussy so you can pound that one too."

Mary's words lit a fire in Caleb's balls. He grabbed Lily's waist to steady himself and began to hammer her cunt. Mary grabbed his head and turned it so that she could kiss him while Lily cried out in joy. It didn't take long before she sprayed her juices around his shaft and across his thighs and balls.

He didn't let up as Mary lifted a tit to his mouth and pressed her nipple into it. She squeezed to make her milk spray into him as he sucked. Mary held her tit up with one hand and reached between his legs with the other.

She found his balls and rolled them around her palm. Again he felt Lily's cunt spray her juices, but this time her cunt clamped even tighter. A constant stream of grunts erupted from her lips punctuated by the occasional attempt at an out of breathe screech. Time seemed to fall away from him. There was only the piston hammering of his cock, Mary's milk giving tit, her hand on his balls, and the love she conveyed to him with her eyes. He only stopped sucking her nipple to kiss her soft lips.

Mary was an older version of her daughters, though still youthful in appearance. Where Kathy had a plump ass and a bit of chub on her belly, her soft skin was taut and firm. Mary was thicker all over. A true MILF, her curvy skin plush and inviting. Her thighs were thick, her ass round, her arms warm and welcoming.

Of all the older women in his harem, Mary's body was his favorite, even surpassing his mother, a feat he once thought impossible. The way Mary looked at him as they kissed was just like her youngest daughter, able to convey her love with a twinkle.

He removed one hand from Lily's hips to grab Mary's ass and pull her closer. Her huge plush tits pressed into his side as he fucked the hucow in front of him.

June saw the way her son held and kissed Mary and she felt a stab of jealousy. She moved to his other side and pressed her own body against him while whispering, "Kiss me too, my sweet boy."

He turned to his mother and recognized her jealous look. He took his hand off Mary and put it back on Lily's hip so he could turn and kiss his mother.

But she didn't want just a kiss. She tugged his arm, and lifted his hand to her own breast. He took the hint and felt her up, while trying to keep fucking Lily. Mary didn't help when she pressed her tits even harder against him. He barely registered Lily cumming over and over again as he kissed back and forth between his two favorite MILF's.

He almost didn't feel it at first, the pressure building in his balls. He thought Mary was squeezing them, but it was them swelling as they prepared to launch his seed. Mary turned her head and hollered, "He's gonna blow girls. Get ready."

June tugged Mary around while Amanda, Roberta, and Amber hurried over to his side and got down on their knees. Five pairs of tits crowded around him as he felt his balls contract and cum fire up his shaft. He slammed himself as deep as he could into Lily's burning hot fuck tunnel. She screamed as his cum splattered against her womb.

Still with a hand on his balls, Mary felt them pulsate once, twice, thrice. She pulled him back and grabbed his slick cock, jerking him as she aimed this way and that to cover the women around him in his delicious spending. She grabbed Amber's hair and pulled her head right to his cock tip. He laughed as Mary got a bullseye right in Amber's left eye.

She shouted, "What the fuck!" as she pulled away.

June laughed, "Everyone gets his cum in their eyes Amber. It's your initiation. Now your part of the family."

She wiped what she could out of her eye and stuffed it into her mouth. After she swallowed she griped, "You could have warned me."

Mary giggled, "That wouldn't be any fun now would it?"

Then she leaned forward and began to slowly lick his cock clean. She took her time but when she was done, June said, "Okay Honey, are you ready to breed Connie now? Or do you need a moment. Perhaps we could put on a show for you?"

Mary had done a good job cleaning him up. So good that he never went soft. He smiled at his mom as he stepped behind Connie and said, "Nah, I'm good. Besides I want to take my time with Connie. I've wanted to do this for years."

He pressed his cock into her and said, "I'm not going to ask if you want a breeding or not Connie. As your bull, I've decided I'm going to cum in you whether you want me to or not. No lube, no vibrators, no massagers. If you wont look at me or talk to me, then I'm going to treat you like a fuck toy. I'm going to fill you with so much cum it will be swimming in your womb for years. Every time you ovulate you're gonna get pregnant with my child. Is that what you want?"

Connie whimpered as his cockhead spread her lips and the tip popped in. "Mount me Caleb. You can breed me as much as you like. I want your cum. I want your baby. Just fuck me like you did Lily."

He grinned as his cock stretched her out. He was really going to enjoy being a bull.

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