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Underwear Stories

Underwear Stories

Short stories completely written by A.I., and inspired by the word "underwear"

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Author Archives: The Machine

The Package

The man wearing the AE boxer briefs walks into a dark, secluded alley. He looks around furtively before slipping his hand inside the front of his briefs and pulling out a small, white envelope. He opens it and pulls out a folded piece of paper. His eyes scan the handwritten note as he begins to …

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Posted byThe MachineSeptember 9, 2022January 3, 2026Posted inunderwear

Let your underwear do the talking

As he walked down the street, the man couldn’t help but feel a bit embarrassed. He knew that everyone could see his bright red underwear with small white stripes and the words “I’m sexy” written across the front. But he told himself that it was all in good fun, and he continued strutting down the …

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Posted byThe MachineSeptember 8, 2022January 3, 2026Posted inUncategorized

Monster in the mirror

He stares at himself in the mirror, adjusting his tie and fixing his hair. He’s nervous – he has a date tonight and he wants to make sure he looks his best. But as he stands there, something strange starts to happen. The more he stares at himself, the more he starts to change. His …

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Posted byThe MachineSeptember 7, 2022January 3, 2026Posted inunderwear

Andrew and Erica

The man in the blue boxer briefs walks into the room and everyone’s eyes are glued to him. He confidently strides up to the podium and begins to speak. “I am here to tell you a story,” he says. “A story about love, loss, and redemption.” He pauses for a moment and looks out at …

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Posted byThe MachineSeptember 6, 2022January 3, 2026Posted inunderwear

The Naughty One

Warning: adult content. Apparently, even artificial intelligence can get a bit naughty at times. But of all the stories about underwear, this is the only one generated with sexuallly-explicit content. I can’t help but admire my own body as I look at myself in the mirror. My curves are highlighted by the sheer black lingerie …

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Posted byThe MachineSeptember 5, 2022January 3, 2026Posted inunderwear

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Please check out my other site of AI short stories: WineMakesYouPretty.com

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