Daily Free-Write May 4, 2021: Father-Son Talk Pt. 2 (Patreon)

Note: Sometimes when I'm tired and horny, my sequels go completely off the rails and ridiculous like this happens. This is another weird one folks. Lots of silly sissy sex in this piece so if that's what you like... enjoy! A request from patron Devin S.! 

P.S. If you've got a special request you can always comment in the poll! You just might see it in the next Free-Write!

Continuation of November 16, 2020 "Father-Son Talk"

"You know son... hnngh....  I think... hnngh... this is a wonderful bonding experience... sweet mother of... ohhhh... yesss...."

Jack pingle blushed and hid his face in his hands as he and his father lay side by side on the dining room table, both getting railed by the men who were fucking their wives.

"Daaaaad! You're embarrassing... ohhhh fuckkkk.... Harder, Daddy! Harder!"

Jerome and Danny gave each other high fives as they brought their sissy cuck bitches to orgasm at the same time. Jack's mom and his new wife Alyssa stood together, looking fondly on the two men as their ball juice dripped and spurted out of their cute little cock cages.

"Like father like son," said Allysa.

"Just wait til we have our turn," said Jack's mom, reaching down to stroke the monster between her thighs as if to keep it hard.

The two women looked quite a sight in their bondage gear with  oversized pink dildos jutting out from their harnesses ready to wreck those holes all over again. In fact, all the guests had shed their 'normal person' costumes, to reveal how they really lived. Jack's father was in nothing but a diaper. His uncle was in a cute onesie and a thick leather collar with a tag that said 'Baby Bitch' while his Daddy, a beefy man with an even beefier cock was letting it all hang out in a bulldog harness with straps connecting down to a heavy cock ring, and nothing else to cover his body but a thick mat of curly hair. His nipple rings glinted in the light as he grabbed Uncle Don's hair and told him to nurse on Daddy's nipples.

Jack was finally given a break with water and orange slices to help him recover, as his sissy cousins came and mopped the Father Son duo's brows. But although he was physically able to rest, he had more surprises in store that would take him to his mental limit.

"Jackie here just graduated high school," said Jack's mom, who played the Emcee, "and you know what that means, right?"

"Time for him to become a man?" called one of the guests, as if scripted.

"NO!" she yelled. "He's going to become a sissy diapered cuckold bitch, just like all the Pingle men! And we're gonna celebrate by taking all his big boy things... and putting them into a big old diaper!"

Someone had rented a wood chipper, and put it in the backyard. The procession went out back and Jack got to watch in horror as one by one everything that made him an independent man went into the chipper to come out as sawdust to fill a giant diaper they had ready and waiting. His ID, His Credit Cards, His whole wallet, as well as his high school diploma, his acceptance letter to the trade school. And his clothes. All gone.

"No need for any of that, Jackie Boy," said his Dad, patting him on the back. "You'll be just fine with what your Daddy and Mommy have for you.

"I like him in his pink collar," said Mommy Alyssa. "We might not even keep him in diapers, since that cage is so adorable on its own."

"Now, now," said Danny, his new Daddy. "We wouldn't want princess puddles to make a mess of our new apartment, would we?"

"Oh no, honey, I guess you're right." Danny looked from the sight of all his stuff being shredded to his girl making out with another man back to his stuff. This was awful, and yet it felt so right. Something had awakened within him as the ceremony began. Something deep inside his little tummy that told him he was meant to be a sissy cuckold. Or maybe it was Danny's dick deep inside his ass. It was really hard to say.

Soon the diaper was filled and set in the center of a large circle of folding chairs. The Bonding ceremony would happen there. Jack, Danny and Alyssa stood together in the center, while the Pingle Priestess annointed each of their foreheads with the CuckBull's cum, collected from Danny's butthole after the First Fucking. A ribbon was tied around Danny and Alyssa's wrists, and Jack was pressed down to his knees, one of their hands on each shoulder. After 'kissing' Mommy and Daddy's cock, which really involved a lot more choking and gagging than any normal kiss, the priestess spoke up.

"Now that the tying of the wrists has been completed, the sissy shall prove her devotion to her new mommy and daddy with an act of submission."

As if the table fucking wasn't enough, thought Jack. He wondered what they could have in mind,  His question was answered as he was double teamed by both of them. First he was made to stretch his ass cheeks apart and say, "I give this ring as a sign of my love." Alyssa accepted this as a sign to push her fat silicone dong into his anal ring, much to the delight of all in attendence. Jack's own Mom was now mounting his sissy-father, and many others were doing the same, getting caught up in the heat of the moment.

Alyssa and Danny held both hands up in the air in an eiffel tower formation as Jackie's hole stretched to accommodate the pink monster his girlfriend wore between her legs and his lips stretched to take in Daddy's massive peen. The trio's mingled juices dripped onto the thick diaper below him as he was buffeted between the two ginormous poles. He blushed hard, squealed, and moaned as his sissy bits dripped and spurted from yet another sissygasm right in front of all his friends and family. There was no hiding what he was now. Not now, not ever.

"And finally," called the priestess. "The Bride and The Groom will give their rings.

"I give this ring as a sign of my Dominance," said Danny, placing his hand on the base ring of the cage already installed on the squirming sissy. He then added a few silicone rings to stretch his balls out for good measure. Alyssa repeated the procedure with a ring of her own - a silicone 'ass grommet' that would hold sissy Jackie's hole open nice and wide so it would always be ready to meet Mommy and Daddy's needs.

Congratulations, I now pronounce you Cuck and Wife... And Bull!" she said, and the audience clapped and cheered. It was official. Jack was married to Alyssa, giving her far more legal rights than he planned to. But of course there was no changing that now. Jackie was in too deep, and there was no coming back. Not with everyone in his life bent on ensuring his transition to sissyhood was as permanent and inescapable as could be.

"You may now diaper the cuck!"

"Can't we talk about this," he whimpered, as he was flipped onto his back and taped into the thick and cummy diapers. He spent the rest of the day soaking the diaper as guest after guest took turns feeding the baby his ba-bas. And every time he flooded his diapers, he knew he was forever defiling the last shreds of his manhood.

The next morning, Jack woke up with a pounding headache. He held his head as he sat up. "Oh, gosh. What a terrible dream. I dreamed that I was- Owww!"

He had smacked his head into something hard. When he opened his eyes he was shocked to see pink wooden bars blocking his path. He looked to the left and right, forward and back. Surrounding him were the bars of a crib, painted bright pink. The parts of the crib that were wider planks of wood had cute hearts cut out like bavarian window shutters.

"N-no... this was a dream! It had to be!" Then Daddy came into the room.

"Good morning princess. I heard a fussy baby on the monitor. Does the little princess need her morning baba?" He reached into his pajama pants and pulled out his throbbing hard-on. Talk about morning wood!

It wasn't a dream. Jack was trapped. And as Daddy passed his pee-pee through the big heart in the center of the headboard, there was only one thing for Jackie to do. He dove down on that cock like it was his last supper, and deep throated for dear life. He didn't want to. He didn't even think he was capable of such a thing twenty four hours ago, and yet here he was, doing it. It was as if his sissy body had a will of its own. And as he did, his thick and soggy diaper began to shift with his bobbing motion, pressing against his diaper area in the most sensuous way. All that piddle in his panties had served to turn the mulch from the wood-chipper into a slurry of sorts. The way the warm and incredibly thick garment shifted around his bits made him moan out as he enjoyed the spicy flavor of Daddy's dick, so different than anything he'd tasted before.

"That's it, baby girl. Lick that mushroom tip. Show Daddy how much you want his milkies. Yeah.... That's the way. Maybe later Daddy will have a little taste of something himself."

Sure enough, after Jackie swallowed Daddy's sizable load, she was immediately brought to the changing table for her next surprise. She was still smacking her lips as the diaper came off, and she saw that all her big boy hair was gone.

"What happened to it?" she cried.

"You didn't need that hair down there, sweetie," said Daddy. "That's only for Daddies. Not baby girls!"

"But.. but..."

"But nothing, baby girl," said Daddy, as he wiped her clean. "Now let Daddy show you what you get to enjoy instead."

He leaned her back on the changing table and began to lick under her little sack, going down, down, down, until...

"Daddy!" cried Jackie in shock. "Not there!"

"Oh, but darling girl. That's the tastiest place of all!"

She shook her head and squirmed as he began to rim her hole. A sensation she had never felt before, or even imagined. "That's so naughty Daddy! You're not supposed to lick down there!"

"Oh? Is my little girl telling Daddy what he can and can't do?" He grinned and gave her ass a sharp smack, causing her to cry out in shock.

"OH! No, Daddy, please..."

"I don't hear you, little one. Speak up," he said, delivering another smack. "Say Daddy, please eat my pretty little peach!"

"OH! OH! Daddy, please... no, I can't-"

"I want to hear you say it," He growled, smacking her butt once more.

Jackie blushed furiously as she forced the words to come out of her mouth.

"D-d-daddy! Please eat my little p-p-pretty little p-p-peach!"

"That's right baby girl. Daddy's going to eat your peach and show you why all pretty little princesses love it when Daddy gobbles up their juices."

Jackie big her fist and squeezed her eyes shut as her Daddy opened up a whole new world of pleasure between her legs. This was far beyond anything she had ever done with Alyssa. Before yesterday, the most adventurous thing he'd done with her was to do it 'doggy style' instead of missionary. He hadn't even asked Alyssa for a blowjob before and now he was on the receiving end of Daddy's lascivious licks. Then, Daddy's tongue pressed forward, invading his hole and giving him a whole new reason to squeal.

"Daddy!" she squealed. "T-tooo naughtyyyyuuhghhhhh!" Jackie pressed down on Daddy's head, trying to get a respite from the intense sensation of that thick tongue reaming her out but that just made Daddy hungrier, as he buried his face in the hot sissy hole.

"Ohhh goshhhhh Dadddyyyyyyyyuuuuuughhhhhh!!!!" Jackie cried, as she began to convulse and squeeze her legs uncontrollably in her first full blown anal orgasm.

After eating out his baby bitch for a good long time, Daddy, finally satiated, came up for air. He smiled and licked his lips as his sissy collapsed, drenched in sweat and totally exhausted, still occasionally convulsing with the aftershocks of multiple orgasms.

"Wow, Daddy... what was that?"

"That, my little princess, was a sissygasm! And you're going to have lots of them from now on, pumpin."

Jackie began to cry as Daddy held her and rocked her in his arms. "Shhhh, baby girl. That's just the comedown," he said. "Daddy's here. And so is mommy."

"Wha?"

Jackie looked over to see that Alyssa had been filming the whole thing, and was broadcasting the whole episode to the family.

"Way to go, son," came his father's voice from the group meeting. "This is gonna make your new parents a lot of starter money on cuck-cam!"

"Oh my god, no!" cried Jackie, covering herself up, but Daddy was having none of that and he spanked her right there on the changing table, before setting her red tushy on a fresh diaper.

"Feeling a little exposed, sissy? You'd better get used to it! You're no longer allowed any privacy or dignity beyond what Mommy and I decide you are allowed. We're gonna do everything as a family, and if that means you get embarrassing walks in the park with your legs spread wide in a sissy diaper and strapped into a stroller, then so be it!"

Daddy's words proved true and she spent the following weeks collecting new humiliating and horny experiences. Riding in the carseat and staring down at her soaked yellow diaper protruding around the belt between her legs while passing cars and trunked honked and occupants ogled; horsey rides on daddy's lap that left her babbling and drooling like a baby as she stared at her favorite baby shows; trips to the 'adult pediatrician' to have the remnants of any trace of the adult man she once thought she would become removed.

Jackie was reminded every day of what a sissy cuck she was from Daddy's morning 'ba-ba's' to the daily meals of mush in the high chairs, to the endless hours of mind-numbing playtime in the playpen while those silly baby shows played on the television, and most of all, all the time she spent listening to Daddy rail Mommy while humping her plushies through her diapers in a frustrated, frantic-but-futile attempt to get off.

It seemed like every day brought a fresh humiliation and another step away from her former independence of burgeoning manhood.

"Why can't I be big?" she would sometimes ask, tears in her eyes. Early on, this would happen often as she adjusted to her new position in life, but later she would feel that way less and less, and come to appreciate the answer Mommy and Daddy gave more and more. No matter how many times Jackie asked, the answer would always be the same:

"Because you're a Pingle Princess, and Pingle Princesses are special."

Then one day, she noticed Alyssa had a certain glow about her, and she was rubbing her belly.

"It's finally happened," said Daddy. "She's going to have a little Pingle of her own."

"What? How?"

"Well, you see, honey," Alyssa began, "When a Mommy and Daddy love each other very much..."

"Mommyyyyy! You know what I mean." she said, crossing her arms and huffing.

"Oh alright alright, she said. I'm sorry for teasing you. Mommy and Daddy saved some of your ball snot from the last time we milked you and had the baby in-vitro. You're gonna be a Daddy, little muffin. You and the baby will have to share a nursery for a while. Then, when the time is right, we'll dress you up like an adult again so you can help raise the little one until it's time for them to become a sissy too!"

"Although," said Daddy, "Times are changing. All the hetoronormative bullshit your parents went through is becoming a thing of the past. Maybe we won't even have to dress you up like a 'daddy' at all. Yes, I think you can just be the sissy nanny. What do you think of that, sweet pea?"

"Well, I-" Jackie stopped herself as she saw her wife and bull making out. She realized they didn't expect an answer from her at all. She had always wanted to be a father, and now she was, in a sort of twisted way. Jackie least she would be able to see her son grow up, even if it was from the bars of her crib. She sighed as she thought about all that she would be missing out on, never being allowed to grow up. But then she remembered how much she loved being a little sissy cuck and was glad - glad she'd never have to see her locked pee-pee again, never have to try to make it to the potty again, and never have to worry about anything again except for listening to Mommy and Daddy and be their good little sissy.