Published: November 17th 2020, 7:44:04 am
Jack Pingle was on cloud 9 as he drove his car home one last time from the school parking lot. After a grueling week of finals, he was finally free. Jack had done it. He'd finally finished high school. By this time tomorrow, he'd be moving out of his parents' house and in with his girlfriend, to their first apartment. He felt like he had gone from being a boy to a man.
He parked his car in the driveway and hopped out. He whistled and spun his keys on his finger as he walked toward the front door.
Inside his mom was already home from work.
"You're home early, mom!"
"I wouldn't miss this day, it's a very special day for you, Jackie!"
Jack frowned at the childish nickname. His mother almost never called him that anymore, thank goodness.
"By the way, how did your finals go?"
"Who cares! I'm done! It's not like I'm planning to college. I'll go to trade school and Alyssa can do her computer science stuff. It'll be great."
It was his mother's turn to frown.
"Oh, Jackie. With an attitude like that, it's no wonder the Pingle men need special treatment."
"Mom, what are you talking about? You've been acting mysterious all month with cryptic remarks about destiny and coming of age."
"Oh don't worry about your mother's ramblings sweetie, I'm so proud of you. Come here and give me a hug."
He came over to her and gave her a big hug. Then they heard Dad coming in, whistling much like his son.
"Hi Dad! Why do you... have... all those bags? Is that a collar? Is somebody getting a pet?"
"Honey," said his Mother. "Why don't you go upstairs and wait for your father."
Jack shrugged and walked up the stairs. He didn't know what they were planning but he figured it was something good. He was finally an independent adult, free of school, free of everything. And he was going to start living that way. He put his arms on his head, elbows out and fell back on the featherdown comforter. He sighed as he sunk down. He hadn't had a good night's sleep all month with finals and all. He smiled as he imagined his life with Alyssa. He'd go to trade school. She'd get a job in computer engineering. They'd have a kid. Maybe a dog. A big dog, probably, judging by some of the stuff he saw Dad carrying in. He imagined playing with the dog, wrestling the bright yellow tennis ball from its mouth and throwing it. He had nearly fallen asleep when he heard a soft knock on his bedroom door. He sat up as his father came in.
He sat up, got up off the bed, and opened it.
"Hello son. I'm sure you're wondering why your mother told you to go up to your room and wait for me."
"Well, yeah, I figured-"
"Let's sit down, son," said his dad, in a soft voice. He walked past Jack and sat down on the bed, then patted the space beside him. Jack sat down next to his father.
"It's time we had a talk, son. You see, all the men in our family are sissy cuckolds."
"They what?" said Jack, with an incredulous laugh. His mouth was open in a smile of surprise. He couldn't believe what had just come out of his Dad's mouth. But his dad wasn't laughing.
"You may be wondering why your mom always laid out my clothes for me in the morning. Why we don't sleep in the same room. And why she has her personal trainer over so often?"
"Well, I mean, I just thought she was... And... uh... J-Jerome... He’s... just... really dedicated..." This was an awkward conversation. Jack was quickly becoming very uncomfortable with the subject matter.
"You may be wondering why your girlfriend insisted you don't go to college after high school. Why she always buys your clothes, and tells you when to go to bed, what to eat. What not to drink..."
"Well, I mean... she's helping me get my life on track. We plan everything together, it's just..." Jack didn't know what to say. He just let out a laugh.
"There's going to be a lot of changes in your life now that you're leaving the house. And you might not like all of them. But just know that this is something that all the Pingle men go through at your age. You should have seen your Uncle Don on his coming of age day. He-"
"Dad, this joke has gone far enough," said Jack, his tone becoming more serious. "Now what's going on, you and mom and the whole family have been acting very strange. Even Alyssa has... wait. This is some sort of weird cult, isn't it? Is my family involved in some weird demonic pact or secret society or something?"
His father just smiled and patted his son's knee.
"It's okay son. You're in the Denial stage. But you'll learn soon enough. Alyssa and Mommy are already downstairs setting up for the ceremony."
"Ceremony?"
"Of course! This is the start of your new life after all. Now keep an open mind. You'll have to get used to your new chastity cage. And you may have to wear diapers. It's up to Alyssa and your buck... that'll be the man that she picks to cuckold you. But if you need to talk to anyone as you get used to living the life of a sissy cuckold in chastity, you can always talk to me or your uncle."
"Wait, you mean his roommate-"
"Yes, that's his Daddy."
His favorite uncle. It all made so much sense now. Why he always seemed to have time to spend with the family. Why he always smelled like baby powder. And why his beefy roommate was always hanging around nearby. They were attached at the hip. They even went to the bathroom together...
"Wait, are you telling me he wears diapers too?"
"He's not the only one son." His dad stood up and unbuckled his pants, letting them drop to the floor.
"Dad, no!" said Jack, raising his hands to shield his eyes, but when he caught a glimpse of something bright pink, his eyes were drawn in and he couldn't look away.
"Dad... why are you wearing a pink polka dot diaper with ponies on it?"
"I've worn these for years, my boy. They're really quite comfortable once you get used to them!"
"No, no, no..." said Jack, running his hands through his hair. He covered his eyes and flopped back on the bed. "I don't want to be a locked sissy cuckold."
"Well," his father said, with a shrug, "that's too bad. Because you don't get to decide. Now just lay right there and let me put your chastity cage on you. Trust me it'll be less embarrassing than being caged in front of the whole family downstairs."
His dad was holding a box that looked like a ring box but opened to reveal a bright pink and impossibly small cage.
"Dad! I'm not wearing that!"
"Yes you are, son. It's up to you whether you do it now or you do it later, but you're gonna put this on sooner or later. Hey, but I'll tell ya what." His dad gave a conspiratorial grin. "If you want, I'll let you bust a nut right now - for old times' sake. This might be the last chance you get!"
"NO! DAD! THAT'S GROSS!"
His Dad shrugged. "Suit yourself. Maybe you'll get lucky and learn to cum getting fucked by your buck."
"Get. Out."
Jack stood up and crossed his arms. He closed his ears to any more of his father's pleas.
Eventually his Dad gave up and left. Soon after, a large man Jack had never seen entered the room with Alyssa.
"Hey there, little man! Names Danny. But you can call me Daddy. Your Papa told Mommy and me that you were being a cranky pants. Do you really want to start off this way with your new Mommy and Daddy?"
"What the hell! Alyssa, who is this?"
"Jackie, be a good boy and let me put the cage on you. Come on, everyone is waiting!" she said it in her schoolgirl whiny voice that they used so often in roleplay, only now her hands were beginning to explore Danny's crotch. His eyes bugged out to see a huge outline snaking down the leg.
"Dude, are you getting off to this? You two are freaks! Get out!"
"Don't talk like that, little man," said Danny, who closed the distance in three short strides and grabbed the boy's wrist. He pulled Jack over his lap and before he knew it the man's rough hands were raining down on his ass, warming it from a sizzle to a searing pain in only a few strokes. Danny screamed and struggled but he was no match for the larger man. Once all the fight was spanked out of him, the man threw Jack over his shoulder and carried him downstairs.
"Oh Jackie, you see how silly it is for you to fight Mommy and Daddy?" Alyssa's voice rang out as they came down the stairs to a big reception.
There, laid out on the dining room table were all the coming of age gifts from friends and family. The unifying theme was pink. Pink diapers. Pink Mitts. A pink collar. Pink leather chastity shorts. And of course, his pink chastity cage waiting for him open on the table.
"Okay everybody! It's time for little Jackie's transformation! Let's give him encouragement as he begins his new life as Alyssa and Danny's locked sissy cuckold baby!"
Jack bawled as he was stripped of his remaining clothes. The crowd cheered as his new Daddy picked up the cage and grabbed him literally by the balls. Daddy smiled and whispered into Jack's ear. "I'm sure going to enjoy fucking Alyssa and my new baby girl. Don't worry. I've got plenty of energy to keep you both satisfied."
Jack's cock was as hard as diamonds, despite his total antipathy to everything that was happening.
"Ice! Can I get some ice over here?"
His cock shrunk down quickly at the cold touch of the ice, and the man easily slipped his balls and flaccid penis through the ring. The pink tube quickly followed and with the turn of the key, his life as a free man was over. Alyssa came up behind him and circled the collar around his neck, pulling it tight. Another click. Another step into permanent cuckold status. She kissed him on the cheek and giggled, then reached over to get the next item. What came next had him squirming and struggling to get off the table, but hands reached out to hold him steady.
"It's okay sweetie!"
"Shhh, just let it happen."
"Oh you'll be so cute in diapers, Jackie!"
A thick pink polka dot diaper was bought out of its bag by Alyssa and unfolded in front of him. She looked down at it and bit her lip as if she was watching a sexy striptease. Despite his best efforts, the diaper was slid under his ass. Danny kissed Alyssa on the mouth in a long deep open mouth kiss, then turned to Jack with a grin.
"Time to pop the sissy's cherry!"
Jack's eyes went wide as both Alyssa and Daniel pulled their pants down. A thick hard meaty rod pointed at him from between Danny's legs and an even larger pink silicone dildo jutted out from between Alyssa's legs. He barely noticed his hands being slipped into his new pink mitts and locked.
"Okay, baby boy. You get one choice today. Who do you want to fuck you first?"
Jack whined. His hole twitched in anticipation. His body was reacting to the transformation. He was turning into a true sissy cuckold.
"D-Daddy..." he said, in a high-pitched voice.
"That's my baby girl!" said Danny, beaming with pride as someone slid the can of Crisco his way. "Just relax, little one. Daddy's gonna make you feel so good you won't even miss using your little clitty like a big girl."
Jack closed his eyes tight waiting for the inevitable. He let out a whisper that perhaps only the few people closest to him could hear.
"Yes, Daddy. Thank you."