Catching Up With The Ex (Patreon)

"I'm not wearing that. No way," said Landon. He stood in front of his ex, Kass, with his pants down around his ankles. She had messaged him about having some post-breakup fun. Against his best judgment, Landon went. All he wanted was some more time with her...well, that and sex. It was a weakness of his and Kass knew it.

"Oh come on, it's just a diaper. Plenty of people wear them. Besides, they're so much fun to play around in," said Kass. She sat on the edge of her bed, a pink-and-white striped diaper unfolded on her lap. Next to it was a pacifier gag among other things than Landon avoided looking at out of embarrassment.

"How are they fun?" Landon asked; once again against his best judgment. It was never good to encourage Kass. She had a habit of getting her way.

"Well…they swaddle a tiny dick like yours so well. And when they get wet...trust me, baby. You'll love how it feels all warm and squishy against your parts," Kass explained. "Remember when I would jerk you off with my wet panties? Imagine that but a thousand times better."

Landon wanted to protest her description of his genitals, but deep down he knew it was true. Landon had always worried he left Kass unsatisfied. Granted, she broke up with him when she found out she was a lesbian. Landon ignored the thought. "So I have to...go in them? I'm not into pee stuff, you know that…"

Kass groaned. "Oh my gosh. You want me to fool around with you, or do you wanna go home and hump your pillow like you probably do every night?"

Landon didn't speak; instead, he gave a very shy nod. It was clear he was unsure, but he was still very much in love with Kass.

"Good…now be a good little boy and lay down so mama Kass can pamper you."

Landon did as he was told. He closed his eyes for the majority of the change. Kass easily flicked away his boxers and shorts and quickly replaced them with the thick, poofy diaper. The thick, poofy material crinkled loudly as Landon squirmed atop it. The smell of baby powder filled his nostrils and the next thing he knew, he was taped snugly in the diaper. "Now back up. And stand in front of the mirror."

Kass had always been the dominant one. It was hard for Landon not to immediately obey.

"Shirt off," said Kass. She then tossed him a pink piece of clothing. "Then put that on. But don't look at it 'till you're wearing it."

Landon did as he was told. Naked save for the diaper, Landon ran the clothing over in his hands until he got it right side out and determined it was a shirt; more specifically, a crop top. He slipped it on over his head and looked at himself in the mirror. The pink and white diaper forced his legs apart into a noticeable waddle and the crop top labeled him as a 'Pamper Sissy' in bright sparkly font. "P-Pamper sissy? I'm not a sissy! I'm not wea--"

Kass was suddenly behind Landon. Her bare breasts were pressed against his back. With her right hand she stretched the waistband of Landon's diaper open and with her left she dumped the contents of a glass down the front of his diaper. The warm liquid was quickly absorbed into the padding. Landon's semi-erect cock was then surrounded by warm, squishy padding. "Oh? Not a pamper sissy, huh? You're not a total diaper loving dork that wants a mommy to rub your diapers?" Kass stroked his cock through the wet padding as she spoke. He rapidly grew hard and began to moan as Kass tended to him.

"N-Nuh…" Landon barely protested.

"Say it and mommy will let you hump to your heart's content.

Landon was putty in her hands. "I'm a pamper sissy. I'm...I'm mommy's diaper dork...please let me make humpies…"

"Such a good little sissy. Mommy will let you make humpies, but first...the sissy needs the rest of her outfit." Kass removed her hands to fetch the items she needed. To her delight, Landon remained in front of the mirror, his eyes fixated on his soggy diaper crotch as he vigorously rubbed himself. "First...we need the sissy nice and obedient. I bet your old collar will help with that, won't it?" Kass slipped Landon's collar around his neck. Back when they were dating, Kass had talked him into pet play. She had also talked him into a pink collar. At the time Kass had said she wanted him wearing her favorite color, but that wasn't true at all. Once the collar was locked in place, Kass knelt down and stretched a pair of locking, frilly panties out at Landon's feet. "Step in, sissy."

Landon was too busy stroking himself to care what it was. Kass had been right, the collar had put him deeper into subspace. He'd do anything Kass wanted.

Click

"Wha-Wait? What's that, mo--uh Kass…?"

"Mommy was right, baby. You're gonna call me mommy or mama from now on. And now that I've got you locked in your pretty panties, you're going to be my obedient little pamper princess from now on."

Landon froze. He stared at the frilly, pink polka dot panties and whimpered. His fingers fumbled with the lock but it was no use. "Wait. No. This is just for fun. Just t-tonight right?"

Kass laughed. She pulled out a pair of locking pink mitts and snapped her fingers. "Hands out. No more grabbing like a big boy."

"But Kass!"

"No buts, sweetheart. Mittens now. Then we can get your tutu on and we can talk about your new life as my little plaything."

Landon didn't resist as the mittens were forced into his hands and locked in place. Then, all he could do was whine as Kass brought the pink tutu out and slipped it up his thighs and over his diaper. "Oh...sorry, forgot. Sissies can't talk like an adult without permission. So it's time to start paci training you."

"Paci traini--mmmmph!" Landon's words were stopped short by the sudden intrusion of a large pink paci gag in his mouth. Much like the rest of his new garb, it was locked in place by Kass.

"When I can trust you'll start acting and talking like a good little sissy, we can remove the gag and keep it pinned to your dress. In the meantime, you'll be dressed like this while I break you in. Shouldn't be too long. You've always been such an eager little thing."

"Mmmmph! Buh guh!" Landon babbled. The nipple of the pacifier was quite large. So much so that Landon couldn't form a single coherent word.

"Sissies don't need big girl words, do they? No…" said Kass, "...sissies make stickies in their wet pampers and thank their mommy, don't they?"

Landon turned from the mirror out of embarrassment and faced Kass. Kass was naked save for her panties. Even nearly nude, Kass felt fully in control of the situation and Landon himself. In her hands she held a butt plug and a tiny pink cock cage. Landon whimpered when he saw them.

"Don't worry, baby. These are for naughty sissies that misbehave. I prefer to spoil my little princess. Go on. Hump your new boyfriend, sissy." Kass stepped to the side and revealed a large teddy bear positioned on the floor next to the bed. "Mr. Bear will be in charge of your stickies from now on. No more pretending to be a man, an adult, or anything else." Kass then leaned in close and gripped Landon's cock through the damp padding. "Go on...be a good sissy and crawl on over to Mr. Bear. Show him how much you love your soggy pampers."

Landon felt truly pathetic and horny beyond belief. His legs felt weak and he fell to his knees mere moments after Kass commanded him to. Landon's diaper crinkled loudly as he closed the distance and, before he knew it, he straddled the bear. He pressed himself into the stuffie and let out a soft moan. Landon surprised himself. He knew he was straight. Sure he was submissive, but he was no diaper loving sissy. And yet...Landon started to hump. He lowered himself until he embraced the bear in a tight hug and began to vigorously hump his new boyfriend, Mr. Bear.

Kass stood and watched Landon with delight. She had, of course, recorded the whole thing. Even when Landon regained his senses in the morning, he would still leave waddling in a soggy diaper with his new boyfriend under one arm and his diaper bag under the other. It had all been a part of Kass's plan. Sure she preferred women, but sissies were just as cute. This way she could keep Landon firmly under her thumb and still have all the fantastic girl dick she wanted. "That's it, sissy. Make big stickies for Mr. Bear. Once you're finished you'll get your night time spankings and a bottle. Maybe mommy will even take that paci out so you can suck on her nipples. I'd say you could pretend to be a big boy again but I doubt you could possibly feel big or boyish after cumming in your pretty pink pampers, isn't that right?"

Landon was in the midst of one of the most powerful orgasms of his life. Halfway through his humping, he had given up on his pride. He was far too horny to care then. Landon would grind and hump Mr. Bear until he made stickies, moaning and whimpering around his pacifier as he did so. Never again would he call himself a real man. Kass and Mr. Bear both made sure he knew all too well what a big pamper sissy he truly was.