wittlesissybaby
Haunted Mansion
Published: October 31st 2023, 2:56:10 am
“See?” Annie said, squeezing Luke’s diaper beneath the frilly skirt. “No one even notices!!”
Luke had begged to differ. He felt like every single eye was on him, even the fake ones from the animatronics and masked decorations.
The party was lively though, so maybe the group of college girls and boys didn’t notice a boy their age was walking in with a dress, pigtails, and an oversized diaper. Maybe they don’t even think I’m a boy at all. He hoped.
“Awww!! Who’s this little cutie?” One of Annie’s friends grinned. She was dressed in a sexy leather catsuit. If Luke wasn’t so mortified by his own outfit, he probably would have had a much more pointed response to hers. With no regard for human social norms, the girl reached between Luke’s legs and groped his diaper. “Seems like a little somewon is having fun in there!” she teased, sipping from a red Solo cup.
Luke flushed in shame. He didn’t notice he was hard until he felt her fingers squeezing his penis around the padding, or was that what made it hard? He never had that kind of response time, but it had to be that, right?
“I’ve always thought beta bois look better in dresses,” the girl said with glazy eyes, “better than trying to cosplay as a real man.”
So she did know he was a boy. Luke hoped the several layers of make-up would have helped hide his ‘masculine’ features. Then he realized he was cursing himself for not looking more like a female.
“Drink up,” The girl said, handing him the rest of her solo cup, “Sowwy it’s not in a ba-ba for the wittle baby!”
Her and Annie both laughed while Luke attempted to drown his shame and sorrow with what was left of the alcoholic punch.
“Come on, loser” Annie said, taking Luke by the hand, “I need to show you off to more of my friends!”
And so she paraded him around the Frat house. Making him curtsey and lift up his skirt for anyone and everyone that wanted to see and ‘check’ his diaper. It was only a small relief that he hadn’t had to actually use the diaper yet. But almost every encounter ended with him finishing the drink of whoever he just flashed his pampered rump to.
“And to think,” Annie hissed in his ear on the way to another group, “If only you’d studied a little harder, I’d probably be in the same outfit sucking your dick right now.”
Don’t remind me. He thought. Annie was Luke’s friend from highschool. They’d had quite the rivalry throughout their Academic career. Eventually, it got to the point where they began competing as to who could get the higher score on exams. It was good for both of them, as the competition only made them better students. It wasn’t long before they began putting stakes on it.
They started out small. $5-$20 bets and such. But by college, they became a little too broke to be shelling out cash for every round of exams. So their stakes became much more creative. Annie had to shout in front of the whole lecture hall that Luke was better at Chemistry. While Luke had to hold a sign under the overpass saying “Will work for bettur English Lit scorez”.
Things quickly snowballed into more, though, as these things always do. The slightly sexual tension became elevated.
“If I win, you give me a handjob.” Luke proffered one day. He expected Annie to laugh it off, or ridicule him for even suggesting it. But she agreed on the condition that she get a 1-hour massage.
“Does this even count as ‘hand’-job?” she asked after she got a 93 to Luke’s 96 on the US History exam. “I mean…I’m only using 2 fingers and you–ohp! Are you cumming already??!”
She never let him live that one down.
“I made your little shrimp dick cum in less than a minute!” she teased. “That thing should be in panties! Or DIAPERS!”
And sure enough, he was wearing a lacy g-string to lecture after the Economics exam.
But the coup de grâce came at midterms.
“Okay, this one has to be big.” Annie had said excitedly. “We’ll take all our exam scores and average them out. Winner takes the cake.”
“And what exactly is the ‘cake’ this time?” Luke asked with a smile.
Annie considered for a while, then shrugged. “Hmm, I dunno.”
There was a lingering silence for a bit while they contemplated. Luke had nothing. He was still happy about the lie he got her to tell all of her girlfriends. The one about him having a ‘very girthy 7-inch dick’. The looks he got from them after that made his chest swell.
“I got it!” she said, “What is your biggest sexual fantasy?”
Luke considered for a second. He didn’t really have one. Well, he did. But not one he could really share.
“Hmm…schoolgirl, I guess.” He shrugged, throwing out something haphazardly. In truth, anything sexual would have been a win for him. He hadn’t had much action other than the two-finger tug from Annie a few weeks prior.
“Is that it?” she pressed, giving him an incredulous look. “No other fetishes I need to know about?”
“No.” He said quickly. Probably too quickly.
Annie continued to stare at him in disbelief. “I saw your browser history when I was uploading that Ethics Essay.”
“What?? I don’t know what you’re–”
“You like girls in diapers.” Annie said, cutting him off before he could feign ignorance.
“Adults in diapers.” Luke clarified for the record.
“Obviously,” she said, rolling her eyes, “You may be weird, but you’re not a fucking p3dophile.”
Luke appreciated her understanding. He expected it to be a lot weirder to be caught having pictures of adult women wearing diapers and humping large teddy bears.
“Okay so you want me to wear a diaper for you, is that it?”
“And the schoolgirl outfit.” Luke added, liking the idea.
Annie nodded as if that were obvious. “Anything else? You just wanna see me prance around in pampers?”
Luke shrugged again, feeling like he was asking for too much.
“You want a blowjob don’t you?”
He could only laugh at how easily she could read his mind.
“That’s quite the tall order,” she said, smiling a bit, “Good thing I’m positive that I won’t be losing.”
“Oh yea? Well if you’re so confident, watta you want then?”
“The same thing.”
“What?”
“The same thing.” she repeated resolutely.
“You want to wear a diaper and a schoolgirl outfit and give me a blowjob? What’s the point of even waiting until the midterms then?”
“No no.” she smiled, “I want you to wear the outfit. And the diaper.”
Luke’s mouth gaped for a second. “Are you serious?”
“Yep.” Annie said without hesitation. “And since you can’t give me a blowjob, you’ll just have to wear it on Halloween.”
******
Well, as you probably deduced by now, Luke did not win that bet. Even though he scored better on 3 out of the 5 midterms, his English Lit score was low enough to bring his average down to the point where it wasn’t even close.
Damn you, Mary Shelley! He’d cursed. Why does Frankenstein have to have so many weird-ass words??
“Pull’em up, pansy!” A girl dressed like Alice in Wonderland said. She also had a chains around her neck and wrists, and was standing with a man dressed as a box. It must have been some clever costume he didn’t get. “Show us those pull-ups!”
“Doesn’t feel like 7-inches in there…” Hermione said after poking his pampers with her wand. “Have you wet it yet?”
“No ma’am!!” Luke replied in the high-pitched voice Annie made him use.
She looked severely disappointed. “Drink up, then!” she said, handing him her cup.
******
“So, which one of these dicks do you want to suck?” Annie asked him.
Luke stopped moving, oblivious to the stares he was getting.
“Awww!! What’s the matturr?” she cooed, “Afraid to hold up your end of the bargain??”
He was speechless, he tried to find the words, but just stood there babbling and stuttering.
“You want the construction worker’s cock in your mouth? Or the sexy fireman? I bet he’d use his hose to pump a big load down your throat. Or do you want–”
“Annie,” Luke said firmly, “I’m not gay.”
Annie burst out laughing. Luke wasn’t sure if it was because of the situation, or she didn’t believe him.
“Luke, I’m kidding.” she said, placing a hand on his, “I’m not gonna make you suck a dick…unless you really want to!”
“Are you guys cumming?” a drunken girl barreled into them, dressed as a sexy bee. (A bee? Yes, apparently they make ‘sexy’ bees now.)
Luke had to shake the thought of sucking cock from his mind. “Wh-what?”
“Coming. Are you guys coming?”
“To what?” Annie asked.
“Haunted House!” the bee screamed, way louder than was necessary. “Sigma Chi! Let’s GOOO!!” and she buzzed off.
Annie crooked an eyebrow at Luke.
“No.” he said firmly, “Absolutely not.”
Luke always hated Halloween. It traced back to the movie…well…Halloween. He still has a specific, vivid memory of walking in on the film just as Michael Myers was brutally stabbing his sister. Young Luke was screaming and crying at the TV before his mother found him. She promised to never tell a soul about how wet his pants were, or how big the puddle on the floor was. Still, that movie traumatized him more than anything else in his life. He woke up with nightmares–and wet beds–all throughout middle school. To this day, he refused to watch horror movies, worried he might have a similar accident even at the age of 21.
“Ohhh come onnn!!” Annie pleaded, “It’ll be fun!”
“No. Out of the question.” Luke said, trying to be as firm as any man wearing a skirt and diaper could possibly be.
“Awww…what’s the matturr?” Annie said, putting on that patronizing voice again, “Is somewon scared they’re gonna have a wittle accident??”
Luke’s stomach dropped. “Did she tell you?? Did Mom really tell you?”
“Tell me what?”
“That I used to wet the bed. That I used to have accidents around Halloween in highschool.”
The shocked look on Annie’s face told him he had said too much. His mother kept her word. She hadn’t told a soul.
“You…what?!”
Luke immediately jumped into damage control, “No no no! Wait!”
“In highschool?!” She shrieked, “Are you really that pathetic??”
“No! NO! I’m not…”
“Is that why you like diapers? For your widdle beddie byes?”
“Annie stop. Please. I–”
“We have to go now!” she said, convinced.
“I…I can’t…I’ll…”
“Scared you’re gonna have an accident?”
Luke wanted to cry, but that would only make him look even more ridiculous in this outfit. “No. I don’t have ‘accidents’ anymore. Stop. Just…”
“Prove it to me.”
“What?”
“Prove it to me.” She repeated. “Prove to me that you can make it all the way through the house without having to wet your widdle baby diaper.”
Luke bit his lip. He hated how this was going, but he also wanted to prove to her–and himself–that he was past all that.
“Fine.” He said, “But if I do. You never mention this again.”
“And if you don’t?”
Luke shrugged, thinking. “I…have to wear diapers for a week.”
Annie shook her head, “Na…you’d enjoy that too much.”
“I don’t like wearing diapers, I like seeing girls wear diapers.” he corrected.
“Well you look like a girl wearing diapers. Does that count?”
Luke wanted to retort, but didn’t feel like he really could at the moment.
“If you make it through with a dry diaper, I’ll give you your schoolgirl blowjob.” she said.
Luke’s ears perked up, he’d hated how much he fantasized about that scenario ever since it had been broached. “Deal.” He said, trying not to sound too anxious. “And if I lose?”
“You will give a schoolgirl blowjob.” she said, without even a hint of a joke.
“I…what? You’re serious?”
“Very much so.”
“What the fuck? Why?”
She shrugged. “I dunno. Ever since I joked about it, I can’t get it out of my head. I can’t help…fantasizing about it.”
Luke could only nod. He knew the feeling. But how hard could it be? He had to go through a house without peeing? Easy money.
“Fine. Whoever loses gives a schoolgirl blowjob. But if I win, you wear a diaper while you’re blowing me.”
“I’ll wear a wet diaper if you win.” She said.
Luke instantly felt himself get massively erect. Well, as ‘massive’ as he could possibly get.
“Alright alright, don’t cum yourself.” Annie laughed, apparently noticing his face, “Sticky pampers count too, ya know.”
Luke hastily agreed to their terms. But as she dragged him by the hand out the door, he already felt a very pressing need coming from his bladder…
******
“See? It’s not so scairwee!” Annie teased.
“That’s because we’re just outside.” Luke said, trembling.
The house was more imposing than he expected. The entire front of the House was covered in black. He probably wouldn’t have even noticed it from the street if it weren’t for the flashing lights and dry-ice smoke wafting through the winds.
“Come on, little one!” Annie said, taking him by the hand.
She slowly led him up the sidewalk. He felt like a child being forced to go to the dentist. She practically had to drag his Mary Jane shoes across the concrete.
“You’re not wet already are you?” she asked, peeking a finger into his diaper.
He wasn’t, but he certainly needed to be. The walk from Frat House to Frat House only made his bladder hurt with every step. All those stupid drinks were hitting him now. It didn’t help that the jungle punch was making his head spin, subsequently making all the ghouls and ghosts spin.
“Now you be a brave little girl,” Annie said, tapping his back affectionately when they reached the door.
“W-wait.” Luke said, snapping out of his cowardice for a second, “You’re not coming with me?!”
“Oh no, dear. You’re going alone!” Annie grinned, “But don’t worry! I’m sure wittle baby Lexi can handle it! I’ll meet you on the other side to check your diaper.” she said, and before Luke could say another word, she was gone.
Luke cried out to her several times, but she just ignored him. Drunk college trick-or-treaters down the block laughed and shouted–probably at him–but he paid them no mind. Instead, he looked up at the ever imposing door.
He reached a trembling hand to the knob, and turned.
The door let out an exaggerated creak. The inside was pitch black. What he hoped would be a loud cacophony of sounds to distract him was instead dead silent.
“Hello?” he called as he stepped in, ignoring the fact that he sounded like every cartoon character stepping into an old, creepy abandoned house.
He tiptoed in further, boards creaking with every step, his diaper crinkled with every step. The light from outside bled in. There were shapes dancing on the walls, but it might have just been his imagination. He could see just enough to notice a stairwell on the right side. That probably wasn’t the best way to get through the house, so he went the other way.
BAM!
The door slammed shut behind him. Luke just about jumped out of his shoes, yelping like a frightened female.
Probably just the wind. He thought.
No longer able to see his hand in front of his face, Luke tip-toed forward. He heard taps and skittering along the walls, but again, that could just be his imagination, or his teeth chattering. He didn’t know what lay before him, but this had to be the route to take. Moving slowly was only making his bladder pulse even more. He was on a ticking clock, he had to get going.
Gulping, Luke gathered up the courage to make prominent strides forward. Into what, he didn’t know, but there wasn’t time to decide.
His diaper was the loudest thing in the room. The urge to pee felt like it was building exponentially. He’d heard from somewhere that if you need to pee, try to think about cumming instead, or vice-versa, one will reduce the urge of the other. So Luke closed his eyes and tried to focus.
Annie was on her knees in front of him. Her pigtails bobbing back and forth, her tongue dancing in her mouth, poking out of her cheeks. The schoolgirl outfit complementing her body perfectly. She swished her diapered butt side to side. It was poking just beneath her skirt, absolutely soaked with piss.
Luke placed his hand on the front of his own diaper. His real diaper. Feeling his erection growing inside. He rubbed it up and down, pressing his palm into it. This was helping. It took the focus off his bladder, giving him a different urge to–
AGHHHHHHHHHHHHHHHHHHHH!!!!
Someone wailed.
Lights went up.
Brightness stinging Luke’s eyes.
A woman in a bloody nurse’s outfit standing in the corner, covered in gore, pulling the intestines out of a man in a hospital bed. Laughing to herself maniacally.
Luke cowered backward, eyes wide, unable to tear his eyes away from the gruesome scene. But out of the corner of his eye, another shape came into view: a clown carrying a chainsaw.
Fucking clowns.
Why did it always have to be clowns?
He turned on his heels, running the only way he knew he could: up the stairs.
The clown was almost on him. Panic pulsed through his veins. Fight or flight engaged. But to him, it was only flight. If there was ever someone that could fly, it would be Luke from how much he was waving his arms in fright.
His scream was high-pitched and frantic, but he didn’t care. He reached the landing of the stairs, only for another imposing figure to block the way. He turned back to the scary-ass clown, half-way up the stairs. Not wanting to fuck with that, he turned back around into the unknown. The figure at the top was gone.
Without stopping to think, he clambered up the steps on all fours, diaper squishing between his legs.
Lights were flashing. Red and white. Red and brown. Red and black. Black. White. Strobed.
It was too chaotic. Too much for his feeble brain to process.
He tried the door in front of him. Locked.
Tried another one. Locked.
The third one swung open, only to reveal two girls dressed as the twins from The Shining. A movie he refused to watch, but had heard enough to know it was not for him–and neither was that room. He slammed the door shut to muffle their demonic “Red Rum” chants.
Another door.
WRRrrEEeEeEeeeeeeeEEEEE
Banshee. Or something. He didn’t know, he didn’t stay long enough to look.
Footsteps behind him. Or were they in front of him?
His diaper long forgotten. The urge to pee nowhere in his mind. The only thing he could think was “get the fuck out”.
He thought about going back the way he came, but that sick-ass clown was waiting at the stairwell.
His only choice was more doors down this never-ending hallway.
Finally, he found a bedroom. A nice, quiet bedroom. White linen sheets, and an open window. Breeze fluttering the curtains.
He closed the door behind him. Trying to take a break and let his heart-rate settle. No chance. It probably wasn’t coming down any time soon. Still, he sat on the bed and took several deep breaths. He diagnosed his diaper, still dry, somehow. Why did they have to make these places so fucking scare–
Hiss!
A rough hand gripped his ankle by the ruffled socks. Something was under the bed. The poor ‘actor’ probably got kicked as Luke scrambled back to the door he came from.
Locked.
FUCK!
The only place to go was out the window. It took very little convincing. Luke never clambered through a narrow rectangle so fast in his life.
He was on an awning now. He could see other parties going on from this vantage, all oblivious to the horror he was going through. He thought to call out to them, but attention to his dress and diapers wasn’t something he needed more of.
The awning wrapped around the house, too high for him to jump down to the ground. Instead, he found another open window.
Such a stupid fucking idea. He thought. A Haunted House?? Annie’s gonna be gargling my balls by the end of this.
The room he climbed into was, ironically, decorated like a nursery. A melodic lullaby playing from somewhere inside.
He walked to the crib, drawn to it, like it had a tractor beam.
He leaned over. There was something on the mattress. A blanket? No, too small. Paper. It was paper. Luke picked it up, squinting at the scratchy writing.
Don’t turn around.
He didn’t listen.
A giant, bloodied teddy bear with glowing eyes towered over him, raising its arms to the sides, long, curved claws scything outwards.
It was terrifying to probably anyone that hadn’t seen it, but Luke had. Well…kinda.
The bear somewhat resembled the ones he’d seen countless women humping in their piss-soaked diapers–minus the fake blood and glowing eyes.
The nursery, the diapers, the bears, all of it spun into this whirlwind of memories. The Halloween scene with Michael Myers, the puddle on the floor, the night-terrors, his mother whispering it’s not real…it’s not real…it’s not real.
Luke looked up.
“You’re not real.” he said, laughing.
The big bear looked caught off guard, confused, most people had probably run away screaming at this point.
But not Luke. He stood strong, resolute in his dress and diaper. “You’re not real.” He repeated. Turning on his heel and striding proudly to the door in his crinkly pampers.
Something tried to jump out and scare him when it opened, a ghoul of some sort, he barely even flinched. The little creaky tricycle from Saw led him to another staircase. This one winding down to a sign that read EXIT in big green letters.
He did it. He conquered his fears. All of this seemed so silly now. People dressed ridiculously, shouting and screaming in hopes of getting other ridiculously dressed people to do the same. He was hardly bothered by the zombified hands reaching for his legs as he descended the steps. He’d done it. Nothing could stop him anymore.
His pigtails swished when he got to the landing and turned around just before the exit. “You’re all a bunch of FREAKS!” He yelled, turning his diapered bum around, hiking up his skirt, and flashing the lot of them.
He was still laughing when he turned around and bumped straight into a pillar. It was embarrassing, but it was also softer than a pillar should be. He craned his neck upwards, only to see a ghostly white mask with hair sticking out the top.
Michael Myers.
All of those images instantly came flooding back, and Luke flooded his diaper so bad he could feel it running down his legs, forming a warm puddle on the floor.
“Awww!! Poor wittle Wexi made a wetsy!!” came Annie’s muffled voice from somewhere. It wasn’t until the man in front of her pulled the mask off that he realized:
Annie was wearing the mask. Annie was Michael Myers. Annie made him wet his diaper.
“Come on, little one,” she said, laughing at the pitiful sight before her, extending a hand, “Let’s go find you a dick to suck!!”
The End
Happy Halloween Everyone!!