Is it Really Humiliation? (Patreon)

“Steph please, let me go!” Jack struggled against the enchanted stocks he had been placed in; he should’ve known to avoid Steph since their breakup, but when she asked to see him it had seemed genuine, “People are gonna be here soon!”

Steph just smirked at her helpless ex-boyfriend. A nice public place like the mall was perfect for his humiliation. His head and hands stuck forward and his rear end stuck up and out with his ankles shackled to the ground, he looked every bit like he was being punished in the medieval days, “I intend for people to see you Jack...and use you as well.”

Jack panicked, wondering just what a witch of Steph’s power could possibly have in store for him, “Oh, here’s Jack’s first patrons of the day!” Jack squirmed in the stocks, desperately trying to get a glimpse of who Steph was mentioning, “Hi girls! Out on a shopping trip?” Jack could only see their faces if he strained hard enough. They seemed to be college types, judging by what they were wearing and how young they looked. He cringed at the thought of three beautiful women seeing him so.

“Yeah! We were just on our way home actually.” Jack shivered as he felt Steph’s hand rest on his backside, gently tugging the waist of his jeans slightly down past his hips and revealing his black boxer briefs underneath, “Awesome! I bet you bought some really cute underwear!” Jack could see that one of the women raised her hand, a tall blonde, “I did; they’re adorable. I just had to wear them out.”

“What if I told you, you could see them magically appear on my pathetic ex-boyfriend here?”

Jack reddened in embarrassment as they laughed, finally taking full note of him in stocks behind Steph, “Okay, I’ll bite. How?”

“Just spank him; no worries, he deserves it.” Jack’s eyes widened in disbelief as more laughter could be heard, “He’s not going to cum or anything is he?”

“Probably, he’s a pretty big sissy.” Getting annoyed with Steph’s jokes at his expense he shook the stocks aggressively, “I am NOT a sissy!”

This only caused more laughter at Jack’s expense, “Hmmm...well if you can refund me for the underwear then I’ll give spanking your ‘not’ sissy boyfriend a shot.”

“Deal!”

Jack groaned in displeasure.

smack

“No, no, no. This is my EX-boyfriend; you need to punish him. Spank him as if he were one of your ex-boyfriends.” More laughter.

SMACK

“Ow! What the hell Steph?! Tell them to lay off!”

“Oh wow! What cute panties you’re wearing...what’s his name?”

“Oh who? My sissy ex-boyfriend? His name is Jack.”

“What cute panties you’re wearing Jackie…” Jack shivered as he felt two fingers running along the inside of the frilled waistband of the panties he now wore. He could feel the restriction to his cock and balls from the tight cotton and felt ashamed as he grew hard as the waistband was snapped against his skin, “...you have to tell me where you shop.”

The stranger and her friends had walked over to the other side of the stocks to get a good look at their victim, laughing at the look on his face. The tall blonde lifted her shirt and revealed a pair of black boxer briefs, “Looks like between you and me, you have far girlier tastes, huh?”

“Oh hey, girls, before you go be sure to snap a pic!”

“Steph no! Don’t tell them that! You’ve had your fun, now let me go!” Jack could practically feel Steph rolling her eyes behind him as his pants were pulled down slightly further, giving the panties a full inch of visibility to passersby, “Hey Amanda, after you take a selfie with this loser, you mind if I swap?”

“Go for it, I mean he’s going to be getting spanked all day; I doubt he’ll keep my panties on for long.” More laughter from his humiliators and the sound of phone camera shutters going off, “My turn, my turn!”

SMACK

“Noooooooo!” Jack struggled against the ankle restraints in frustration.

“Oh my gosh! So cute!” More fingers reached underneath the band, tugging it upward and causing his crotch to become more restrained; Jack breathed in sharply as he felt the pressure causing his cock to get close to bursting, “Excuse me, miss? Could I call my friends down here? I’m sure they’d get a kick out of your sissy!”

“Sure! The more the merrier; in fact, I’m sure Jackie here would like to personally thank you for that. He loves wearing pretty panties after all, don’t you?” Steph, Amanda, and her friends had all approached the front of the stocks looking expectantly at the helpless, pantied ex-boyfriend.

Jack stared at them all angrily, furious that one of the girls was on the phone calling more people to witness his humiliation, “Fuck off. There’s no way in hell I’m saying thank you for this!”

Amanda looked down at him and shook her head, “Hey Tiffany, you mind spanking the sissy? He seems a widdle cwanky; I think he wants a fresh pair of panties to wear.” The shorter brunette winked at Jack before disappearing around the stocks.

SMACK

“Owww! Stop!” Jack had to calm himself for a moment, or else he would cum. Whatever Tiffany was wearing felt terribly good; the soft fabric of the panties practically made him orgasm off feel alone. He had hoped his sudden change in demeanor would remain unnoticed, but all the women seemed very well aware of it.

Steph seemed absolutely thrilled by the turn of events, “I know why he’s acting up. He loves panties so much; he doesn’t want to soil them with his cummies...” A collective ‘Aww’ went through the group, “...but I’ve got a solution for that.” Waving her hands in front of her, Steph cast a spell on Jack that transformed his clothing completely.

“There you go princess! Now you can make cummies to your heart’s delight.”

For a moment, Jack was confused; but then Tiffany burst out laughing, “Amanda! Sammy! Come look at this; lil Jackie here is wearing diapers! And such a pretty little dress!”

“Oh my god! It barely does anything to cover up these huge diapers; and look at these adorable tights!”

“Patent leather shoes? You really went all out on this sissy!”

Jack had never felt so embarrassed in his life; he never thought he’d be wishing to be put back in frilly panties, but here he was diapered and dolled up wishing just that. He felt a hand grip the crotch of his diaper and he felt himself so close to moaning and giving up; filling his diaper with warm loads of cum.

“Someone’s hard as a rock!”

“I bet he’ll need a diaper change soon!”

Jack didn’t like where this was going; ever since his transformation into a diapered doll, more people had begun to gather around him. Some pointed, others talked among themselves, while most pulled out their phones and began to record.

“Steph please, there are pe--,” Jack’s words were stopped short as Steph stuffed her fingers in his mouth, “Please do explain to me, Jack; why should I let you go?”

“I’m thowy we bwoke up. I’ll oo anyfing oou aant.”

“Wow, you really are great with words Jackie, but…” Steph pressed her fingers down on Jack’s tongue and a wave of pleasure washed through his body. Helpless to fight it, Jack found himself embracing it completely as he moaned loudly around his ex-girlfriend’s fingers and shot his load into the thick padding taped around his waist.

“Oh my god, everybody, he’s cumming. The little sissy is cumming in his diapers!”

Jack only felt more pleasure as people gathered around; his body shook with pleasure as he continued to cum, at Steph’s mercy so long as she held her fingers in place.

“That’s right, just like a little water spout; keep going until you’re empty sissy.” Jack did just that, humping whatever hand was currently inspecting his humiliatingly soaked and diapered crotch.

“STEPH! What do you think you’re doing?” Removing her fingers from Jack’s mouth, Steph turned to find her mother staring back at her, arms crossed, “Is this how you use your magic when I’m not around? Getting off by turning giving your ex-boyfriend his sissy fantasy?” Jack didn’t bother arguing with her.

Steph actually managed to look embarrassed for once, “I’m not getting off mom! And you’re not the boss of me; I’m an adult!”

“Oh is that so? Then why is your crotch so wet then?” With a flick of her wrist, the older witch raised her daughter’s skirt revealing Steph’s damp panties underneath.

“MOM!” Steph desperately tried to pull her skirt back down, but Steph and Jack both knew from dealing with her mother, that Steph was helpless to the older witch’s power. Jack’s eyes widened at the sight, his presumably drained cock rising back to full attention upon seeing his ex-girlfriend’s panties. Thankfully for Jack, several other people took note as well and took their attention off of him for the moment.

“I’ve had it up to here with you lately; you want to act like a clown? Well now you can look like one too!” Steph had little time to wonder what her mother meant before she was surrounded in deep violet tendrils of magical energy. Her somewhat moderate clothing shrunk into revealing, brightly-colored clothing covered in polka dots and stripes. Steph’s loose hair raised itself into pigtails and dyed itself a bright pink. Her face was covered in white and pink makeup and her skirt was transformed into a bright pink tutu that fully revealed her striped panties underneath.

“W-what the fuck mom!”

“You want to entertain people at the mall with your ridiculous shit, well now your wish has come true! A very fitting look for you!”

Steph scowled at her before turning her frown into a sly grin, “Fine mom! You’re right! I deserve to look like this! Hey everybody! Look at me!” Taking a quick run around Jack’s stocks, Steph somersaulted in front of her mother and splayed her legs outward as she landed; face down, her ass was on display for all to see. Steph giggled as she pulled the frills of her tutu away from her panties, “Like what ya see?”

Jack had never seen such flexibility from Steph; and seeing her dressed so ridiculously, in such revealing clothing caused him to start cumming all over again.

“Steph, I want you to know that you brought this upon yourself. I’m only punishing you to make sure you behave yourself in the future.”

“I’m just doing what you made me do mom! What’s the matter? Don’t like clowns? It looks like Jack certainly doe--whoa!” Jack watched as his ex-girlfriend was raised in the air, positioned much like himself, and then imprisoned in a similar stockade, “Yes he does! And he’s going to have a great view of your punishment, too!”

“Mom! You bitch, this isn’t fair! I didn’t ask you to come down here!”

“And I didn’t ask you to misuse your powers, maybe I’ll allow you to have them back when I feel you’re mature enough.”

All Jack could see was Steph’s ass; but he could feel her anger as she shook against the restraints, her ass jiggling as she did so. This punishment was becoming far less so for Jack as things progressed.

“You’re taking my powers?!”

“Already have. Now enough out of you,” Steph’s mom turned to face the growing crowd, “If anyone would like to punish my daughter for her naughty actions please line up, and be sure not to block the sissy’s view!”

Steph rattled the restraints around her ankles and wrists to no avail, crying out as the first woman lined up and spanked her. Jack was in heaven, his cock close to exploding the moment Steph’s brightly colored, striped clown underwear was immediately traded for a pair of pink lace panties. She yelped in pain as she was spanked again and again, wearing different panties of varying coverage and color each time. Unable to help himself any longer, Jack began to cum in his diapers once more, growing terribly aware of just how much he had soiled them with his ejaculate. It felt embarrassing for Jack to admit it, but he was in sore need of a diaper change.

“Mommy! Mommy! Can I thpank the naughty cwown?” A mother and daughter had approached walking hand in hand; the daughter being no more than a few years old. She waddled as she approached Steph’s reddened rear end and began to lightly pat her right cheek.

“Sure sweetie, but you’re going to have to smack harder; she’s been a very bad girl.”

SMACK

Jack couldn’t believe his eyes as Steph’s legs were forced apart by the diaper that suddenly appeared around her waist. It was a thick disposable decorated with pink and blue teddy bear print. He could barely hear Steph’s shocked expletives over her mother’s laughter as she squirmed, the diaper crinkling all the while.

The audience that had gathered was getting full plenty of enjoyment from the helpless diapered sissy and clown in front of them. Many choose to mock and squeeze their diapers, taking pictures and videos; some were too busy harassing the both of them from the front, asking them humiliating questions like if they enjoyed what was happening to them.

Steph’s mother was beside herself with her daughter’s humiliation, “Alright you two, I’ll spare you any more public humiliation; but we’re not done yet.” With a clap the witch, her clown of a daughter, and the pathetic sissy all disappeared from the mall, appearing instantly at Steph’s house in her room.

Steph laid on the floor, her legs raised and spread as she groaned; Jack laying on top of her, his diapered butt sticking in the air. Steph’s mother stood nearby, a satisfied look on her face as she looked at her humiliated victims, “I don’t know why you two ever broke up; you’re practically made for each other.” With a snap of her fingers, Steph’s mother entered Jack’s mind and filled it with thoughts of sissy actions, Steph, and diapers. Using her hand she controlled him and forced him to crawl off of her daughter. Jack watched with glee as his ex-girlfriend was transformed, her clown appearance altered to better fit her newly diapered lifestyle. The colors of her clothing becoming soft pastels instead of their original neon. Her bra disappeared and her top shrunk, attaching to her shrinking tutu and forming a frilled onesie. The pigtails that adorned her head grew longer and acquired long pink ribbons. Lastly, her mind was altered like Jack’s, rendering her helpless to escape her love of diapers, Jack, and being an obedient babygirl. Before the two knew it, they were kissing each other excitedly; humping each other through their diapers and discussing in crude baby-talk how much they ‘wubbed’ each other.

Using a bit more magic, Steph’s mother transformed her daughter’s room into a large nursery fit for the two of them, “There! You two ought to be much more manageable now in your current state; isn’t that right?”

Instead of answering, Steph pinned Jack to the floor and straddled his cock through their diapers, moaning loudly as she grinded against him as best she could. Jack’s legs were spread and raised upward, revealing the large bulge in the seat of his diaper; judging by Jack’s expression he wasn’t finished with it either.

“I’ll take that as a yes. Alright you two, have fun. Mommy will be back when she’s heard you’ve finished!”

With that, the mother witch pulled the nursery room door to and left the diaper crazed couple moaning on the floor, “Oh god Jack, I wuv being a widdle baby.”

“M-m-me too!”

Steph squeezed his rear end and laughed, “Someone needs a change! Oh! I-I-I think I need one too!” Steph’s whole frame shook atop him as she began to orgasm, “I can’t wait to be a good girl forever! I’m so glad my mommy taught us a lesson!”

Jack arched his back, pressing his padded cock into his girlfriend’s diapered crotch as deep as he could, whimpering as he came one last time into his diaper. The two breathed heavily for a while, their chests moving in sync; soon their eyes began to grow heavy-lidded and warmth spread over their crotches as they both wet themselves in their sleep.

Standing in the doorway, the mother witch stared down at her diapered charges; smiling at just how well things went today. After extensive cleaning and being put into a fresh diaper, the two were placed and restrained in their respective cribs. The mother briefly pondered if she would truly give her daughter’s powers back once she felt her mature enough, but seeing how cute she looked she didn’t think she’d have the desire to ever let the girl back out of diapers.