The Trickiest (Funniest/Sadest) situation you have got yourself while in Cuba?

[JohnnyO]

The story has a hidden message for Havanafest. Stay near the Prez. He's got bail money!

[CanuckSARTech]

LOL. Nice story Rob. Might have heard you jabbering about parts of that during the previous trip. Nice to hear the whole story (or at least your own drunken side of it, LOL!).

Hoping that I don't best any of those hijinks this year! LOL.

The trip in Nov 2012 was interesting when a number of us took a drunken 5am stroll past the U.S. Special Interests building. Which, of course, has loads of Cuban special police standing guard around it, looking outwards, ensuring no Cubans break into it. So, it made it an ass-pucker moment for me when the streets were quiet, but for a couple of drunk and stumbling Canucks, when one of our party started singing "Yankee Doodle Went to Town" (or something to that effect). LOL. We were shadowed for a bit. Luckily, didn't have to pay anything though.

[Strada]

LOL. Nice story Rob. Might have heard you jabbering about parts of that during the previous trip. Nice to hear the whole story (or at least your own drunken side of it, LOL!).

Hoping that I don't best any of those hijinks this year! LOL.

The trip in Nov 2012 was interesting when a number of us took a drunken 5am stroll past the U.S. Special Interests building. Which, of course, has loads of Cuban special police standing guard around it, looking outwards, ensuring no Cubans break into it. So, it made it an ass-pucker moment for me when the streets were quiet, but for a couple of drunk and stumbling Canucks, when one of our party started singing "Yankee Doodle Went to Town" (or something to that effect). LOL. We were shadowed for a bit. Luckily, didn't have to pay anything though.

I also recall trying to hitch a ride from a chicken and/or hay truck back to the nacional...

[Ryan]

Here’s one that is not safe for work, neither is it suitable for people who might be upset at “adult themes”.

My first time in Cuba we hung out in the Gato Tuerto, we got to know a regular there quite well, I suppose she would have been called a jinetera. My Spanish was even worse then than it is now and she had decent enough English, so we tipped her and bought her the odd drink to hang out with us in the bar for a chat and a laugh, rather than head off with a client. If she found a client later in the night, that was her business.

Anyway, we got to know her quite well. The following year, I was heading back, I got an idea for some work for an online magazine to do an interview with a Cuban jinetera.

I called her up, she was very into the idea as long as real names weren’t used. Fine.

We went for a meal, to a place she chose and got to the interview.

Since I had last seen her she had got out of ‘the game’ and was now running a pawn business with her sister in Nuevo Vedado, fair play to her.

Started off with the usual background questions and then got into stuff regarding her previous work. All fairly horrible stuff as you might expect. She got into it at age 18 during the Cuban special period, cried for 3 weeks after her first time. Got back into it at 35 because she needed to pay a $5,000 bribe. Stories of being raped by cops when she couldn’t pay their bribes. Stories that should be printed on a card and given to every male over 18 entering Cuba.

Anyway, I asked her what was the most bizarre thing she ever saw. And here we go.

She got a call from an older European man to join him in his hotel room.

He wanted to pay her and all he wanted her to do was watch him as he shoved a water bottle up his own rear. She was fine with that.

I asked her what size water bottle, she pointed to the one on our table. The standard 1.5 litre bottle of Ciego Montero, everywhere in touristy Cuba. I’d guess about 14 inches high and 3 inches diameter at the base.

He was struggling with it so he asked her to help him.

“I’m not going near that!” she says, so he offers her $3,000 to help him. I asked her if that made a difference, she said she ran across the room to help him.

I asked how far up he managed to get it, she told me there was about 4 inches left sticking out.

She told a friend of hers about this the next day and the friend wouldn’t believe her. So she called up the client and asked if she could go along that night and bring a friend. He was more than willing.

That night, the two of them sat in the room while the client performed the bottle trick on himself again. Then she said “That night, everything in the hotel room went up that man’s ass.”

“Everything?”

“E-v-e-r-y-t-h-i-n-g”

“Like what?”

“Like, the telephone, the stationary, the TV remote, the contents of the minibar, the complimentary toiletries, everything.”

She had a lot of money from this man and of course she was buying goods and food for her entire extended family. Her grandmother was so grateful to this client of her grand-daughter that she asked her to take a present along to him the next night.

“What was the present?” I asked.

“A carved wooden cigar holder.”

“What size was it?”

She made gestures to show me it was about 12 inches long and 2 inches diameter.

“What happened when he saw that?”

“His eyes lit up, he took his clothes off and started rolling a condom onto it!”

So there you go. Not necessarily the happiest story in the world but we both laughed, a lot, as she was telling me that. Tears laughing.

And this was after feeling like getting kicked in the stomach over and over again from some of the stuff she was telling me earlier.

Interesting thing about that night, one of the last things I asked her was would she ever go back to doing what she once did if the need arose.

“No problem.” she said. “I wouldn’t want to or choose to but if I needed to, what else would I do?”

Does that story count as sad and funny?

[...]

Thanks for the story Ryan. Funny bits through it as well. Prostitution is a weird concept and is ripe with horror stories and sadness. Some girls get out of it and make a new life for themselves while others are scarred for life or end up in a body bag. Oldest trade in history they say...

[CanuckSARTech]

I also recall trying to hitch a ride from a chicken and/or hay truck back to the nacional...

LOL. Forgot about that part!!!!

I'll try to do so this year, and will send you a happy picture if I do!!!

[CanuckSARTech]

Amazing story, Andy. Wow.

[Habana Mike]

Here’s one that is not safe for work, neither is it suitable for people who might be upset at “adult themes”.

Anyway, I asked her what was the most bizarre thing she ever saw. And here we go.

“That night, everything in the hotel room went up that man’s ass.”

“Everything?”

“E-v-e-r-y-t-h-i-n-g”

“Like what?”

“Like, the telephone, the stationary, the TV remote, the contents of the minibar, the complimentary toiletries, everything.”

Which hotel? I'm avoiding remotes, phones, minibar contents, toiletries, everything!!!!

[CUBANO]

Here’s one that is not safe for work, neither is it suitable for people who might be upset at “adult themes”.

My first time in Cuba we hung out in the Gato Tuerto, we got to know a regular there quite well, I suppose she would have been called a jinetera. My Spanish was even worse then than it is now and she had decent enough English, so we tipped her and bought her the odd drink to hang out with us in the bar for a chat and a laugh, rather than head off with a client. If she found a client later in the night, that was her business.

Anyway, we got to know her quite well. The following year, I was heading back, I got an idea for some work for an online magazine to do an interview with a Cuban jinetera.

I called her up, she was very into the idea as long as real names weren’t used. Fine.

We went for a meal, to a place she chose and got to the interview.

Since I had last seen her she had got out of ‘the game’ and was now running a pawn business with her sister in Nuevo Vedado, fair play to her.

Started off with the usual background questions and then got into stuff regarding her previous work. All fairly horrible stuff as you might expect. She got into it at age 18 during the Cuban special period, cried for 3 weeks after her first time. Got back into it at 35 because she needed to pay a $5,000 bribe. Stories of being raped by cops when she couldn’t pay their bribes. Stories that should be printed on a card and given to every male over 18 entering Cuba.

Anyway, I asked her what was the most bizarre thing she ever saw. And here we go.

She got a call from an older European man to join him in his hotel room.

He wanted to pay her and all he wanted her to do was watch him as he shoved a water bottle up his own rear. She was fine with that.

I asked her what size water bottle, she pointed to the one on our table. The standard 1.5 litre bottle of Ciego Montero, everywhere in touristy Cuba. I’d guess about 14 inches high and 3 inches diameter at the base.

He was struggling with it so he asked her to help him.

“I’m not going near that!” she says, so he offers her $3,000 to help him. I asked her if that made a difference, she said she ran across the room to help him.

I asked how far up he managed to get it, she told me there was about 4 inches left sticking out.

She told a friend of hers about this the next day and the friend wouldn’t believe her. So she called up the client and asked if she could go along that night and bring a friend. He was more than willing.

That night, the two of them sat in the room while the client performed the bottle trick on himself again. Then she said “That night, everything in the hotel room went up that man’s ass.”

“Everything?”

“E-v-e-r-y-t-h-i-n-g”

“Like what?”

“Like, the telephone, the stationary, the TV remote, the contents of the minibar, the complimentary toiletries, everything.”

She had a lot of money from this man and of course she was buying goods and food for her entire extended family. Her grandmother was so grateful to this client of her grand-daughter that she asked her to take a present along to him the next night.

“What was the present?” I asked.

“A carved wooden cigar holder.”

“What size was it?”

She made gestures to show me it was about 12 inches long and 2 inches diameter.

“What happened when he saw that?”

“His eyes lit up, he took his clothes off and started rolling a condom onto it!”

So there you go. Not necessarily the happiest story in the world but we both laughed, a lot, as she was telling me that. Tears laughing.

And this was after feeling like getting kicked in the stomach over and over again from some of the stuff she was telling me earlier.

Interesting thing about that night, one of the last things I asked her was would she ever go back to doing what she once did if the need arose.

“No problem.” she said. “I wouldn’t want to or choose to but if I needed to, what else would I do?”

Does that story count as sad and funny?

I'm glad we are staying in a Casa.

[madandana]

He has stayed there as well.

[CUBANO]

He has stayed there as well.

Don't tell me that! LOL

[Habana Mike]

Sounds like that dude's had everything in Havana up his ass!

Hopefully not the cigars. Nothing aged for me

[...]

Sounds like that dude's had everything in Havana up his ass!

Hopefully not the cigars. Nothing aged for me

By the sound of it, singles are pretty safe. I'd worry about bundles and 50 cabs though...

Edit: one can only wonder whether that guy was the inspiration behind the latest Cohiba supremo...