wittlesissybaby
Stairway to Hell
Published: August 7th 2023, 3:55:45 am
Jesse knew he should have found a new apartment complex after he and Lauren broke up. Few would advise staying in the same building as your ex, but the place was affordable and it was close to work.
Luckily, he’d managed to avoid bumping into her despite several months of living in the same area. But sure enough, at quite possibly the worst time, he was waddling up the stairs the same time Lauren was heading down them.
“Uh…hi Lauren,” Jesse said awkwardly.
“Hello skidmark.” Lauren said ruthfully, her voice still dripping with disdain. “I heard you got a new girlfriend! What’s her name?”
“M-Melanie” Jesse stammered, feeling extremely awkward and uncomfortable.
“Melanie…that’s right.” Lauren sighed, even though she’d stalked his Facebook long before. “Does she know about your little…interest?”
Jesse eyed side to side like he didn’t know what she was referring to, so Lauren clarified. “How you like to be, shall we say, ‘pampered’?”
He immediately flushed, becoming visibly uncomfortable, like he was hiding something.
“Oh my god!” Lauren gasped. “You’re wearing one right now, aren’t you?!”
Jesse continued to stammer, to try and deny it, but before he could, Lauren leaned over and jerked his pants down. As she suspected, Jesse had a big, pink diaper between his legs, and it was absolutely soaked.
“Oh my godd you are such a fucking LOSER!” she bellowed, wondering why she ever put up with him for so long. “Does she know?? She doesn’t, does she? You were taking a little stroll in your puffy pamper and hoping to get back in time to change before she got home weren’t you?? You used to do that shit all the time with me too!!” Lauren continued to berate him while Jesse squirmed, beet red.
“I’m not gonna let you get away with this. I’m not going to let this poor girl put up with your tiny, pathetic penis for so long, only to find out you prefer stuffing it inside of a pissy pamper instead of a wet pussy!”
He tried to blubber something, but she wouldn’t hear it. “Shut up! Shut the fuck up! You know what we’re gonna do? You’re going to stand over there in the corner with your pants down and your pretty pink pamper on display! And we’re going to sit here and wait for little Melanie to come traipsing up the stairs!”
“N-no!” Jesse finally said, finding his voice. But Lauren wasn’t having it. She grabbed his ear, twisted, and yanked him over to the corner.
“Don’t act like you’re not fucking loving this!” She hissed into his ear. “I bet you’re hard as a rock right now, aren’t you?!”
She didn’t even wait for his answer, she reached around and peeked into his diaper, bursting with laughter.
“Hahaha!! I don’t think I've ever seen you so stiff! I didn’t think your wittle guy could get that big! Now how long until Melanie gets here??”
“Th-th-th-thirty minutes…” Jesse blubbered pathetically, tears streaming down his face.
“Good.” Lauren said, pulling out her phone. “That leaves plenty of opportunity for picture time! I’ve got to show all my friends and family what a pathetic, pampered pansy I used to date!”