"Undercover Hijinks: Busty Wives, Moving Boobs, and a Disastrous Stakeout"
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I nudged my friend in the rib after he had gone to feel his boob one more time and another hand on his ass as well. “Dude, could you try to act like a chick? We’re undercover, remember?” I had to remind him for the 10th time today. We were going undercover as a married couple to spy on my girlfriend while she was on a work trip and he, by some twist of fate and probably one too many beers, ended up as the busty redheaded wife.
To be fair, Jerry had really committed to the role with a fiery red wig, a dress that could make a mermaid jealous, and more padding than a moving company's storage unit. It wasn’t his fault that he felt the need to occasionally check if everything was still in place—or at least that's what he claimed every time he got caught fondling "himself."
“Sorry, Steve. It’s just… these things are everywhere!” Jerry whispered loudly, drawing the attention of a nearby hotel staff member. "I don't know how women handle it, man!"
“You’d better handle it, or we’re doomed!” I whispered back harshly. I mean, it was believable, right? A nice married couple, Ronald and Veronica O’Tool, here to enjoy a lovely weekend getaway. The plan was simple; I needed to know if Linda was cheating on me or not. Nothing complicated. Just good old-fashioned spying wrapped in a ludicrous disguise.
But Jerry might as well have had "undercover" tattooed on his forehead. If our cover was blown, it would only be because he was acting as masculine and goofy as a bull in a china shop.
He adjusted his dress again, swearing as the strap slipped off his shoulder. Jerry, in his full commitment, had listed all the pros and cons of our costume, and trust me, it was a longer list than Santa’s Nice/Naughty list. And by now, I was convinced the cons outweighed the pros—mostly because Jerry had listed “moving boobs” and “tight dresses” as the main pros, which seemed dubious.
My girlfriend, Linda, was inside, supposedly attending a business conference. We trailed her, cautious and discreet. Or tried to be. “Stop making eyes at the bellboy,” I hissed as Jerry made yet another longing glance. “You’re supposed to be my wife, not auditioning for a soap opera.”
“Right, right,” Jerry muttered, pulling himself together. “But Steve, these heels are murdering my feet. Do women have feet made of steel or something?”
“Yes,” I said exasperated. “Steel toes for weapons against imbeciles like us.”
We made our way to the bar area, where the conference guests were gathered. Jerry tried to walk confidently in those heels but looked like he was strutting down an invisible catwalk. Definitely not model material. We're talking more Godzilla meets Bambi.
We spotted Linda sitting with a group of colleagues, laughing and engaging in what seemed to be innocent conversation. Or was it? Clearly, some intense detective work was needed. And by detective work, I mean listening in while pretending to sip cocktails and avoid making more scenes.
Jerry and I took a seat nearby, I ordered a martini, and Jerry went with some colorful, fruity cocktail because "it looked less suspicious." Meanwhile, his grip on his new assets seemed unrelenting.
“That dude from accounting keeps looking at Linda,” Jerry said, almost spilling his drink.
“Which one?” I asked, squinting at the cluster of people.
“The one with the receding hairline and the alpaca sweater,” Jerry elaborated while taking an awkward sip from his straw.
“Oh my God, Jerry! That’s her boss!” I facepalmed. “And her boss’s wife is right next to him!”
“Wow,” Jerry said, recovering from nearly choking on his drink. “She really is faithful to company policy.”
I sighed. At this rate, I’d discover who Linda’s cheating partner was, or more likely, end up in the hotel’s crazy log for suspicion of public indecency or general weirdness.
As the evening wore on, it became clear that Linda wasn’t sneaking around or exchanging secret glances with any mysterious paramours. Maybe I had been wrong about her. And maybe Jerry's obnoxious antics had taught me more about trust and the weirdness of love than a million Jeremy Kyle episodes ever could.
By the end of the night, Jerry had slipped off his heels and was walking barefoot, which meant we'd have to avoid the management at breakfast. But at least we were in this together—well, the weirdest stakeout ever, decorated with one too many fringes and falsies.
“So, still think she’s cheating?” Jerry asked, sagely holding his wig like a wrestling belt.
“No,” I admitted. “But I think you emerged the real champion of this misadventure.”
“Great,” he grinned. “But now you owe me a foot massage, dude. And while you’re at it, a pizza, extra everything.”
This story was generated by user zach3 with assistance by one of OpenAI’s large-scale language-generation model; prompts used to help generate the story are shown below.
Images were generated with OpenAI's AI system, DALL·E 2, or uploaded by the user.
AI Prompts
Prompt: I nudged my friend in the rib after he had gone to feel his boob one more time and another hand on his ass as well. “Dude could you try to act like a chick were here undercover remember.” I had to remind him for the 10th time today. We were going undercover as a married couple to spy on my girlfriend while she was on a work trip he ended up as the busty redheaded wife. I thought maybe we could get closer to her like this but he’s going to end up blowing our cover. I need to know if she’s cheating on me or not. I'm not sure he should've been the woman with how masculine and goofy he is acting. I hope this plan works.
Response: I nudged my friend in the rib after he had gone to feel his boob one more time and another hand on his ass as well. “Dude, could you try to act like a chick? We’re undercover, remember?” I had to remind him for the 10th time today. We were going undercover as a married couple to spy on my girlfriend while she was on a work trip and he, by some twist of fate and probably one too many beers, ended up as the busty redheaded wife. To be fair, Jerry had really committed to the role with a fiery red wig, a dress that could make a mermaid jealous, and more padding than a moving company's storage unit. It wasn’t his fault that he felt the need to occasionally check if everything was still in place—or at least that's what he claimed every time he got caught fondling "himself." “Sorry, Steve. It’s just… these things are everywhere!” Jerry whispered loudly, drawing the attention of a nearby hotel staff member. "I don't know how women handle it, man!" “You’d better handle it, or we’re doomed!” I whispered back harshly. I mean, it was believable, right? A nice married couple, Ronald and Veronica O’Tool, here to enjoy a lovely weekend getaway. The plan was simple; I needed to know if Linda was cheating on me or not. Nothing complicated. Just good old-fashioned spying wrapped in a ludicrous disguise. But Jerry might as well have had "undercover" tattooed on his forehead. If our cover was blown, it would only be because he was acting as masculine and goofy as a bull in a china shop. He adjusted his dress again, swearing as the strap slipped off his shoulder. Jerry, in his full commitment, had listed all the pros and cons of our costume, and trust me, it was a longer list than Santa’s Nice/Naughty list. And by now, I was convinced the cons outweighed the pros—mostly because Jerry had listed “moving boobs” and “tight dresses” as the main pros, which seemed dubious. My girlfriend, Linda, was inside, supposedly attending a business conference. We trailed her, cautious and discreet. Or tried to be. “Stop making eyes at the bellboy,” I hissed as Jerry made yet another longing glance. “You’re supposed to be my wife, not auditioning for a soap opera.” “Right, right,” Jerry muttered, pulling himself together. “But Steve, these heels are murdering my feet. Do women have feet made of steel or something?” “Yes,” I said exasperated. “Steel toes for weapons against imbeciles like us.” We made our way to the bar area, where the conference guests were gathered. Jerry tried to walk confidently in those heels but looked like he was strutting down an invisible catwalk. Definitely not model material. We're talking more Godzilla meets Bambi. We spotted Linda sitting with a group of colleagues, laughing and engaging in what seemed to be innocent conversation. Or was it? Clearly, some intense detective work was needed. And by detective work, I mean listening in while pretending to sip cocktails and avoid making more scenes. Jerry and I took a seat nearby, I ordered a martini, and Jerry went with some colorful, fruity cocktail because "it looked less suspicious." Meanwhile, his grip on his new assets seemed unrelenting. “That dude from accounting keeps looking at Linda,” Jerry said, almost spilling his drink. “Which one?” I asked, squinting at the cluster of people. “The one with the receding hairline and the alpaca sweater,” Jerry elaborated while taking an awkward sip from his straw. “Oh my God, Jerry! That’s her boss!” I facepalmed. “And her boss’s wife is right next to him!” “Wow,” Jerry said, recovering from nearly choking on his drink. “She really is faithful to company policy.” I sighed. At this rate, I’d discover who Linda’s cheating partner was, or more likely, end up in the hotel’s crazy log for suspicion of public indecency or general weirdness. As the evening wore on, it became clear that Linda wasn’t sneaking around or exchanging secret glances with any mysterious paramours. Maybe I had been wrong about her. And maybe Jerry's obnoxious antics had taught me more about trust and the weirdness of love than a million Jeremy Kyle episodes ever could. By the end of the night, Jerry had slipped off his heels and was walking barefoot, which meant we'd have to avoid the management at breakfast. But at least we were in this together—well, the weirdest stakeout ever, decorated with one too many fringes and falsies. “So, still think she’s cheating?” Jerry asked, sagely holding his wig like a wrestling belt. “No,” I admitted. “But I think you emerged the real champion of this misadventure.” “Great,” he grinned. “But now you owe me a foot massage, dude. And while you’re at it, a pizza, extra everything.”
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