wittlesissybaby
Around the Block (Custom Caption)
Published: March 30th 2023, 9:30:01 pm
“Awww!! What’s the matter, Kylie? Is it hard to get around the block in what you have on??”
Kole’s girlfriend or– ex girlfriend–laughed at her own pun. Kole had been getting around the block with several women apparently. Wendy had heard from quite a few people that Kole had been unfaithful. Being employed as the neighborhood gardener and pool boy must have given him an ‘in’. None of his relations lasted very long though, not once they found out what he was packing…
“I can’t believe I put up with your little baby dick for SO long, only for you to last a whole 20 seconds inside of someone else!!”
Kole whimpered behind his gag, attempting to say something but it all came out as muffled mmph’ing. He was probably trying to spin some sort of lie.
But Wendy wasn’t done berating him. “The entire neighborhood knows about your transgressions. Do you have any idea how humiliating that is?
More muffled protests, but this time he couldn’t deflect and gaslight her like he always did.
“Well, you’re about to be just as humiliated as you make your way around the block again!”
She shoved him forward with her foot. Kole stumbled on his high heels. His gait was hobbled and wonky. The massive buttplug she’d inserted probably didn’t make things any easier, but at least he had a nice, fluffy adult diaper to go around it and hold it in. It crinkled along with the swishing and swaying of his frilly dress. She wondered if his shrimp dick was small and limp like it usually was, or if it was throbbing inside its cage. She secretly hoped it was the latter, not only because it would be hilarious if he was getting off to this shit (he did like it when she slapped him around) but also because it probably really hurt when his penis pressed against the metal barbs inside the cage.
The way he squealed and clenched his legs a few seconds later conveyed the answer.
It was a slow, arduous walk. But what better way to commemorate the moment than to video the whole thing on her phone?
“I’m putting this on the NextDoor app!” she laughed wickedly, “ and I’m sure your friends would love to see this!”
He stopped, wide-eyed, turned around, and started desperately pleading behind his gag. It was such a pitiful sight, and made for even better footage.
“Awww! What? Does wittle Kywie not want his friends to see what a pretty pink bimbo he is??”
Kole shook his head so vehemently that the pigtails from his wig smacked him in the face.
“Then you’re gonna have to do something to keep this our little secret.”
“Hmm?” Kole asked as best he could.
Wendy patted her chin like she was just coming up with the idea that had been planted in her mind since before this little ruse even started.
“Well…a lot of husbands in the neighborhood aren’t too happy that you were slipping the sausage to their wives. Vienna sausage, that is. ” she grinned, “But they’ve agreed to not kick the ever living shit out of you as long as you let them slip you the sausage!”
His eyes went wide in terror again.
Wendy laughed maniacally. “Sorry, you don’t have much of a choice. Your first customer is up here at 223 Privy Dr.! Remember Rebecca? Her husband has quite the…bone…to pick with you!”