1 - 20 of 38 Works in Pee-Wee Herman
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Pee-wee swallowed hard as he took another shaky step forward, his heartbeat quickening by every second that passed. The wooden floor underneath him creaked and whined under his feet, no matter how quiet he tried to be, it gave him away as though it was intentional...
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The Day of the Switched-Up Ladies by Dead_Heartbreaker_Boys
Fandoms: Pee-Wee's Playhouse (TV)
22 Sep 2025
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A weird day at the Playhouse
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It's Halloween and Pee-wee sure is excited but when he's about to announce today's secret word, someone knocks on the door and a mysterious creature appears on his doorstep…
- Language:
- English
- Words:
- 3,612
- Chapters:
- 1/1
- Kudos:
- 2
- Hits:
- 11
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A Day Worth To Remember by qopu999
Fandoms: Pee-wee's Big Adventure (1985), Pee-wee's Big Holiday (2016)
13 Sep 2025
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As soon as he woke up, he knew that today was going to be a wonderful day... and he couldn't wait to meet his best friend.
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The continuation of "Pee-Wee's Big Crush."
Pee-Wee Herman has JUST come to terms with the fact that he might have some more than friendly feelings for his new best friend, movie star Joe Manganiello. And that same famous, hunky movie star just invited himself over for a sleepover at Pee-Wee's house. Problem is…Pee-Wee’s never had a sleep over before! Especially not with such a hot, handsome, gorgeous, triple cool star of the big and silver screens!
And if Joe finds out that Pee-Wee has a big, fat crush on him, it will ruin their friendship! After all, someone like Joe would NEVER like-like someone like Pee-Wee Herman, the little nobody from Fairville, back…right?
Pee-Wee Herman/Joe Manganiello
Series
- Part 2 of Pee-Wee's Big Gay Romance
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Basically after watching "Pee Wee As Himself", I wanted to give Pee Wee the coming/love story Paul Reubens wasn’t able to give himself.
Then I revisited Big Holiday (2016), and realized I didn’t have to do much…but I did it anyway!Takes place shortly after the film, and Pee-Wee is still having confusion dreams about his new best friend. They say it takes a village to raise a man-child, and thankfully Pee Wee has a pretty good village in the form of the townspeople of Fairville to help him sort out his big feelings.
Pee-Wee Herman/Joe Manganiello
Series
- Part 1 of Pee-Wee's Big Gay Romance
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Fandom Character Death Match Tournament Bracket 23, Round 4, Match 2: Pee-Wee Herman vs. Forrest Gump by magic8ballzz
Fandoms: Pee-Wee's Playhouse (TV), Forrest Gump (1994)
18 Jul 2025
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In the chaotic Nexus Arena, two wildly mismatched combatants face off in a death match like no other: Pee-Wee Herman, the whimsical mischief-maker armed with boundless energy and his trusty bicycle, and Forrest Gump, the unassuming man whose simple wisdom and unexpected resilience defy all odds. As the arena’s hazards shift and the rules demand blood, this unlikely duel unfolds with accidental chaos, absurdity, and surprising heart. Who will survive this surreal contest of fate, fun, and sheer unpredictability?
Series
- Part 696 of Fandom Character Death Match Tournament
- Language:
- English
- Words:
- 1,265
- Chapters:
- 1/1
- Hits:
- 5
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Fandom Character Death Match Tournament Bracket 23, Round 3, Match 3: Pee-Wee Herman vs. Neo by magic8ballzz
Fandoms: Pee-Wee's Playhouse (TV), The Matrix (Movies)
18 Jul 2025
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In the Crucible of Infinite Realities, two unlikely combatants face off in the ultimate Omniversal Death Match Tournament: Neo, the savior of Zion and master of the Matrix, and Pee-Wee Herman, the whimsical and unpredictable icon of childhood chaos. When reality itself bends and warps around their clash, only one can emerge victorious—but in a battle where logic and nonsense collide, nothing is ever quite what it seems.
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- Part 693 of Fandom Character Death Match Tournament
- Language:
- English
- Words:
- 1,343
- Chapters:
- 1/1
- Hits:
- 5
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Fandom Character Death Match Tournament Bracket 23, Round 2, Match 5: Pee-Wee Herman vs. Casper the Friendly Ghost by magic8ballzz
Fandoms: Pee-Wee's Playhouse (TV), Casper the Friendly Ghost (Short Films 1945-1959)
18 Jul 2025
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In the swirling chaos of the Celestial Combat Tournament, two unlikely contenders face the arena’s merciless decree: Pee-Wee Herman, the eccentric man-child with a laugh that could split dimensions, and Casper the Friendly Ghost, ever-polite and tragically non-corporeal. Locked in a surreal showdown beneath an audience of gods, ghouls, and cartoon legends, the pair must navigate not only the tournament’s deadly rules, but their own irreconcilable natures. Whimsy clashes with spectral sincerity in this absurd, emotional, and cosmic battle of misfits.
- Language:
- English
- Words:
- 1,065
- Chapters:
- 1/1
- Hits:
- 3
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Fandom Character Death Match Tournament Bracket 23, Round 1, Match 9: Pee-Wee Herman vs. Ernest P. Worrell by magic8ballzz
Fandoms: Pee-Wee's Playhouse (TV), Ernest Goes to Camp (1987)
18 Jul 2025
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In the chaotic Multiverse Coliseum, the zany and unpredictable Pee-Wee Herman faces off against the good-natured but clumsy Ernest P. Worrell in a battle unlike any other. Surrounded by surreal Playhouse elements and bizarre arena traps, this clash of manic mischief and accidental mayhem spirals into a wild contest where laughter and chaos might just be the deadliest weapons. Who will outwit, outmaneuver, and outlast in this cosmic showdown of eccentricity and earnestness?
Series
- Part 676 of Fandom Character Death Match Tournament
- Language:
- English
- Words:
- 1,556
- Chapters:
- 1/1
- Hits:
- 6
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Cowboy Curtis always comes by the Playhouse at the same time every Saturday-high noon, like any good cowboy should. He brings stories of the wild west, his boots scuffing the linoleum floor, his hat always one size too cool. Pee-wee greets him with a scream of delight every time like it’s the first time he’s ever seen him. Because maybe it feels like the first time. Every time.
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You and Pee-Wee have already spent quite a bit of time having fun at the playhouse, but it's not long before the two of you begin to grow tired.
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A gay adventure romance
Pee Wee Herman and Mickey Morelli fall in love. As that highway calls so does being on the run together. A thrill that they both dare to chase again. Will they regret it. Who knows. Stay tuned.Series
- Language:
- English
- Words:
- 790
- Chapters:
- 1/10
- Kudos:
- 4
- Hits:
- 64
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Sing Me To Sleep by MelodyEverbelle
Fandoms: Pee-Wee's Playhouse (TV), Pee-wee's Big Adventure (1985)
03 Aug 2024
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When you're struggling to fall asleep, Pee-wee steps in to help.
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We all know the story of Pee-wee going on an adventure to find his beloved bike, but what if his girlfriend Darcie was with him?
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It's Pee-wee and Darcie's wedding day!
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Darcie and Pee-wee are planning their wedding and share a sweet moment together.
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All The Things He Said by PeeweesGayhouse69 (CampCornette69)
Fandoms: Pee-wee's Big Adventure (1985), Pee-Wee's Playhouse (TV)
27 Dec 2023
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An argument in the rain shines light on some hidden feelings for Pee-wee and Francis. What will happen from then on?
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Winter comes to Puppetland, and Pee-wee and Darcie decide to have some fun in the snow.
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Bailando by MelodyEverbelle
Fandoms: Pee-Wee's Playhouse (TV), Pee-wee's Big Adventure (1985)
06 Dec 2023
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During tonight's ball, your friendship with Pee-wee becomes more than that after an encounter with his enemy.