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TIFU by not realizing I was being hustled by Cuban pimps
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JonSolo1 is in Cuba
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This happened in the Obama era when US-Cuban relations were semi-normal, on a trip to Havana.

My brothers and I were on a classic car tour one of the days with a guide and a driver. We’re having a nice time driving around Havana, seeing the sights which I’d only read about in history books, etc., and taking in the sense of feeling like I was in a tropical North Korea and having some heartwarming genuine moments with locals in my broken Spanish.

Then we get to an eclectic neighborhood of the city, and are out of the car walking around. These two guys walk up to us: one was huge and looked like David Ortiz’s twin, and the other one was short and thin. Looking back on it, our guide immediately got a bit of an “oh shit” expression because she clearly knew them, but she tried to roll with it and didn’t tell them to fuck off.

They start walking with us while we’re being shown different things, trying to chat us up, being very broey and friendly, but in a very weird way. They figured we were dumb gringos and David Ortiz (DO) started calling us his cabróns, assuming we didn’t know what it meant and would think it was a term of endearment. My brother immediately started throwing it back at him like “no, you’re my cabrón.” At one point DO even takes my brother’s hat off and puts it on his head, so my brother takes it right back without missing a beat. We go with it and don’t really stand up to them because again, this dude is huge and you have to tread extremely lightly in a situation like that.

Then they ask us if we want to buy their mix tape. They’re really persistent and won’t take no for an answer, so I give him $10 and put it in my bag thinking they’ll leave us alone. Think I threw it out when I got back to my room because it was definitely going to be all sorts of bad shit.

They don’t leave us alone. DO asks us if we want to get a drink with them. We go in a little cafe with one table and nobody else in it but the person behind the bar. The entire neighborhood is empty too. We sit down at the very small circular table, and order a pitcher of mojitos. Awkward, uneasy conversation continues.

DO is sitting right next to me. Little guy isn’t doing much talking. DO taps me on the arm and asks if I want to see his “girlfriend.” I say sure, and he pulls out a 5 peso Cuban version of a Walmart smart phone. He shows me and only me a photo of a naked girl in a shower. I say “nice” and he starts swiping. Every photo is a different naked Cuban girl and then he zooms out to a whole fucking gallery. It suddenly hits me that he’s a pimp, and I try to casually stop looking at his phone. He asks me if I’m an f-word, to which I just didn’t know what to reply. Looking back I should’ve made up an excuse like “no, I have a girlfriend at home.”

We finally get out of there and back to the car with our guide after paying way too much for the mojito pitcher, and the guide sort of apologized but not really.

I’d be lying if I said some of the girls weren’t attractive, but as an American spending a few days in a barely diplomatically neutral land, I wasn’t trying to 1. wind up in a Cuban prison, 2. get an STD, or 3. suddenly change my philosophy on partaking in such business endeavors.

That’s my Cuban pimp story.

TL;DR: while a tourist in Havana, a pair of Cuban pimps took me for a ride

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2 years ago