wittlesissybaby
Say It With Your Cheeks (Custom Caption)
Published: August 16th 2023, 3:47:18 am
“Bend over, bitch. Lift that fucking skirt and show me what I made your wife write on that dumbass diaper.” Marcus ordered.
“Y-yes Master.” The prissy sissy squeaked in that pathetic little voice Marcus makes him use.
Jeremy could hear Marcus and his wife cackling with laughter from the bed behind him.
“What do you think it says on the back of your diaper, honey?” Sandra asked in her sinister voice.
Jeremy trembled, knowing if he answered incorrectly he would be in big trouble. But he knew it was most likely one of two options, Loser or Cuck.
He decided to trust his gut. “C-c-cuck Madame…?”
The silence let him know he answered correctly, they were both probably smirking.
“Someone knows exactly what they are.” Sandra chuckled.
“Is that what you are, bitch?” Marcus barked, “a fucking cuck?”
“Yes Master.” No hesitation, he knew better by now.
“You did a good job cleaning Mommy and Daddy up after we had our playtime.” Sandra mused, “at least your tongue is good for something, so you’re not completely useless.”
Jeremy could still taste the cum on his palate. It was mixed with his wife’s sweet, delicious juices, and Marcus’ dick sweat from cleaning up his cock and balls.
“Would you like a reward for being such a good little cumrag?” Sandra asked.
Jeremy had the most pitifully desperate response. “Yes Madame!! P-p-p-please!”
Was he finally going to get his cage off? He could barely remember the last time he came, he really couldn’t remember the last time he got to do it with his cage off.
“Pull that diaper down, cuck.” Marcus growled.
Jeremy eagerly started tugging down his diaper, and spun around to face them.
“DID I TELL YOU TO FUCKING TURN AROUND BITCH?!” Marcus roared.
Jeremy practically shrank down in fear, cowering like a terrified puppy before quickly turning back to the window. He bent with his diaper exposing his still burning bottom.
“For being such a good little cleanup-queen, Daddy’s gonna fuck your pretty pussy.” Sandra explained.
Jeremy’s stomach dropped as he was filled with a mixture of fear and disappointment.
“Someone doesn’t look too excited.” Marcus shrugged.
“N-no! Master! I am!!” He wasn’t. Marcus had a BIG dick. Sandra could barely handle it, so how was he supposed to?
“Hmm..doesn’t sound like it.” Sandra tutted. “Maybe you should beg.”
Jeremy couldn’t help but let out a whimper…he hoped they wouldn’t punish him for that later.
“M-m-m-Master? Would you please fuck my prissy pussy?” Jeremey stammered.
“Spread your cheeks.” He ordered.
Jeremy reached his painted nails back, grabbing both his ass cheeks and pulling them apart until it hurt. Feeling extremely exposed and vulnerable with his puckering pink rosebud on full display.
“You were saying?” Marcus prompted.
Jeremy sighed exasperatedly, still trembling. “P-p-please! Sir! Will you please fuck my poor little asshole?”
“Don’t ask me with just your mouth.” Marcus said, “Talk outta ya ass. Use both types of cheeks.”
It took a while for Jeremy to understand what he meant, then it hit him. He started pushing and pulling his cheeks together and apart, mimicking a sideways mouth.
“Please sir, will you fuck my wittle asshole.” Jeremy whimpered and flapped his buttcheeks in rhythm with the words.
Both of them roared with laughter, slapping their knees with entertainment. He wouldn’t doubt Sandra was filming the unbelievably pathetic sight.
“Tell him thank you.” Sandra said between fits of laughter. “Tell him thank you for what he did to me.”
Jeremy let out a long blink before tugging on his cheeks again, “th-thank you for fucking my wife sir!” he murmured like a Ventriloquist, “thank you for giving her so many orgasms!” He thought that sufficed, but he decided it was best to slip one more in, “and for giving me that lovely meal afterwards.”
After their laughter finally died, they were silent for a while. Jeremy was desperate to look behind him, but knew better. He heard a *click*. That was the lube, hopefully that was the lube. He was unbelievably relieved when he felt the cold liquid hit his tailbone. She gave it a quick swipe through his crack, nothing compared to how many swipes she had to use when she changed his dirty diapers. But it wasn’t enough, he could already tell.
“More lube!” Jeremy begged as she walked away, “please Mommy!! More lube!!”
But Marcus already had his hands on him, grabbing Jeremy firmly by the waist and moving him where he wanted with ease.
Jeremy was still begging as he felt Marcus’s python probing between his cheeks. When he found it, he pressed it into his hole with very gradual—but always forward—force.
Jeremy let out the most high-pitched squeal, panting as he tried to relax while feeling like he was being split in half.
He felt the pressure on his prostate, that did help ease some tension as his eyes rolled back in his head. His cock had retreated in on itself inside his cage, submitting to the much bigger member now fully stuffed in his hole.
“Ask me again,” Marcus growled in his ear.
“Please…” Jeremy strained. “Fuck me…”
And that he did. Marcus started pounding into him, making his cheeks clap and shake more than they did during his pitiful puppet show.
It wasn’t even going on very long before Jeremy’s breathing changed. Every. Single. Stroke felt like it was poking and snaking into and across his spot. It actually felt good. His ass was more relaxed now, so he tried to focus on the goal.
He bucked his hips back against Marcus. Much to their amusement.
“Harder” Jeremy moaned before he could stop himself, but he didn’t care, he needed it. “please! Harder!”
Marcus grabbed Jeremy’s hips and yanked it over his cock. Plunging himself in deeper and deeper, harder and harder.
Jeremy lost his voice minus the faintest of grunts. Head tilted back, mouth gaping in an “O” as he had a little ‘O’ of his own.
“Did he just?” Marcus stopped. He snapped his fingers at Sandra, she obediently stepped forward, peeking a finger into the front of Jeremy’s diaper.
“Ohhhoho yea!” She exclaimed, examining the damage. She rubbed his back patronizingly, “Awww!! Little cucky made a yucky in his ducky diapurrs!!”
Jeremy had to hide his smile, still panting.
“But you didn’t ask permission to cum, did you?” Sandra leered.
Immediately Jeremy was stricken with fear. His horniness long evaporated, making whatever came next that much less enjoyable.
“Finish up,” Sandra said, tapping Marcus’s bare butt encouragingly. “Then put him over your knee while your cum drips out of his asshole.”