Cuba Libre

This story is based on actual events. Cuba is a great place to visit, even if it's not known for sex tourism like the DR or Thailand are.

I love Cuba.

I had been Cuba for the first couple days of my ten day stay. The resort was all inclusive, and, even though I was paying the premium for solo occupancy, it cost half what a similar place in Mexico would run. The first couple days I took in the lay of the land while lounging around the pool bar and ogling Canadian college girls down on Spring Break. A $20 tip to the bartender each morning, taking care of all the tips for the day, meant he was my best friend. After all, he got paid about $40 per month.

He hooked me up with the guy at the resort (every resort has a guy like this) who had a wife/brother/sister/in-law who worked at a cigar factory. For the price of two such cigars in Canada the guy could get me a box (24) of top-quality stogies right from the factory. He also made sure my drink never got more than half empty, walking my next one over himself each time.

I had watched an odd couple, a young Cuban girl who was arm candy for a fat, balding German guy, during those first two days. I knew the game, but made sure to talk to the bartender. Every resort has a few of these girls hanging about. Someone at the resort gets paid to look the other way, and the girls help attract repeat business from single men, or at least those travelling single.

My bartender friend knew the girl’s name, had an idea of the services, and suggested prices. In Cuba, everything is negotiable. Capitalism in its truest form.

In the third morning, the fat kraut was gone and my prospective senorita was flying solo. I’m guessing the bartender told her I was interested, because she strolled into the pool area, looked around, and walked straight towards my chair.

Maria, probably not her real name but you have to admit a whore named Mary is wonderfully ironic, was a real beauty. Deep bronze skin, long black hair, and a gorgeous face. Cuban women are almost always thin, at least until they have kids, and she was of middling height and slender, but had a decent pair of tits and a nicely curved butt. It’s hard to gauge the ages of these girls. She could have been mid-teens (in looks at least) to mid-twenties.

“Hola”, she said, standing in the perfect spot for the sun to show off her body, which was in a fairly nice skirt and top that showed off her legs and belly while emphasizing her chest. “You look lonely today. Where is your wife?”

I laughed and held up my hand. “No wife, and you know I’ve been here alone the last few days. Where did your friend go?”

She had the most darling little pout. “Yes”, she replied, drawing the word out. I loved her accent, and could not wait for her to talk dirty with it. “He was not much fun anyway.” Like a good sales woman, she turned the conversation back to me. “You to handsome to be single!”

Now, I’m not a particularly handsome guy. Mid-40’s, decent shape but a bit of a gut, hair just starting to grey. Women don’t cringe when they see me, but they don’t turn their heads, either. Maria had that gift that really good strippers have of making you feel very desirable and getting you to ignore that part of you that knows it’s all bullshit. Of course, once your wallet is empty, so is her interest in you.

“Well, you could fix that for me. I bet you are a lot of fun.”

With that, she sat down. Neither of us beat around the bush. I knew what she was, and she knew I knew what she was, so, calling for a drink for her, we got down to business.

I won’t bore you too much with the details of the negotiation, especially not the prices. Depending on the time of year and, quite honestly, how much she likes you, the same girl can have wildly fluctuating prices. We started with how long, the next seven days. The price she quoted me was oral and vaginal. I never bother to talk a girl down, especially because, in Cuba, the US dollar goes a LONG way. Then I started specifying additional services and offered a price. Invariably she would ask for more, and I never quibbled.

Almost anything was on the menu, as long as I would pay. And I bring plenty of cash when I visit Cuba.

When we had finalized our agreement, I summed it up. “I’ll treat you like a queen in public, but like a dirty puta in my room.” Maybe she thought I was kidding. Maybe she thought she could pout her way out of some of what was in store. Or maybe at heart she really was a dirty whore. She certainly enjoyed 90% of it.

One thing to remember if you’re going to make an arrangement like this. Prostitutes want their money up front, but you should only pay a day at a time. That way, she can’t run off with more than a single day’s money, and until the last day, she won’t want to walk away from all the rest, unless you really piss her off. And make sure you have a way to keep her from stealing your money when you’re sitting on the toilet.

Business concluded, we went back to my room.

I was staying in the upgraded area of the resort, so the room was very nice. A sitting area facing the balcony, a king bed, a jacuzzi, and the stand up shower and toilet with doors for privacy. She lay on the bed with a grin, and I just shook my head, and motioned for her to come down by the balcony.

For my money, a whore who expects subtlety can go find someone else. I tossed a pillow from the couch onto the floor, and she knew what to do. Maria knelt down and pulled down my swim trunks while I unbuttoned my shirt. When my cock popped out, she let out a fake little gasp of excitement, “Tan grande!”, which means ‘so big!’. Once again, bullshit, since my cock is decidedly average. But I appreciated it.

Although maybe she meant my balls, because I’ve been told those are huge. Seriously. Weird when a girl admits your dick is average but your balls are the biggest they've ever seen. Such is my genitalia, though. The lucky girls, or at least the girls I get lucky with, soon learn that those big balls produce a lot of jizz.

Maria knew what she was doing, and she seemed to have an idea right away of what I liked. She managed to undress while hardly ever letting my cock out of her mouth, then she really got down to business. She needed to show me I was worth not just the price, but worth paying it for a week.

She did not waste time playing with my dick with kisses and the like. She licked it a few times, staring up at me and putting on a lascivious show. After that, she opened up her lips and oh so slowly pushed her head down onto my cock until I hit the back of her mouth and she gagged. She didn’t pull back right away, forcing herself to keep on choking on my cock.

Damn I love that.

Her fellatio was sloppy, just the way I like it. Her eyes watered, her mouth slobbered, and when she needed a break to catch her breath she was either stroking it with her hand or wiping it across her cheek, smearing the spit and making her face as shiny as her tits were getting.

Ever the romantic, I told her, “Fuck, you’re good!” and meant it. “Just your mouth this time.” With my cock in
her mouth she nodded and said something in response. From that point on, she used one hand on herself, taking care of herself since I obviously wasn’t going to.

She probably figured I’d cum quick, but if so she was seriously disappointed. Even though she gave some of the best head I had ever had, I made sure to enjoy it. I took charge, grabbing her head and fucking her mouth. I was rough, the kind of shit you see in a site like Broken Latina Whores. She choked and sputtered, and when I wanted a break, to let her breathe as much as anything else, I smacked her face with my cock.

I tossed her on the bed, on her back with her head over the edge, and fucked her mouth upside down. This was new to her, and it’s one of my favorite positions. I can get in extra deep, my balls smashed on her nose, and watch her throat bulge as my cockhead pushes down it. If she was faking her orgasm when I started reaching forward and spanking her pussy with hy fingers, she was a very good actress. If you’ve never had your cock in a slut’s mouth while she cums, you’re missing out.

Maria was petite enough for me to lift off the ground. I flipped her upside down and did a standing 69, except I don’t eat pussy I pay for. Instead, I held her against the wall and, with my thighs on the sides of her head and the wall behind it, she had no way to escape as I fucked her mouth like that. Finally she slapped at my ass to get me to let her breathe.

But she did not complain. I must have been paying her a lot more than she normally made.

She didn’t complain when I put her back on her knees and starting jerking off into her face, even when I called her a good dirty little whore. She just tilted her face back, opened her mouth and stuck her tongue out a little while using one hand to play with herself. She squealed when I came, shutting her eyes tight but keeping in place with her mouth open. I make a real mess, and I made sure I got a couple pics on my cell before I let her clean up.

We hopped into the shower together and I asked if she’d like to go shopping. If you’re going to hire a whore for a week, take her shopping as a reward. The more appreciation you show (the more money you spend on her at the mall) the nastier she’ll let you get with her.

As you can tell, I like to be nasty.

We hired a cab, one of those cars from the 50’s, a convertible, that are somehow kept in immaculate shape, for the day. I let her pick a place for lunch. For a Westerner, the biggest drawback of Cuba is the food can be disappointing, but she knew a place that had good seafood. Shopping in Cuba is more a matter of seeing what they have than looking for what you want. Since she had come with the clothes on her back, which were now rumpled, I bought her a couple of outfits and the smallest two bikinis we could find. I told her we’d come back again in a couple of days. If she was a good puta.

I had never fucked in the back of a car. It cost a hundred bucks, but I got the guy to park the car in a nice secluded spot overlooking the water and to take a walk. The rubber went on (if you’re fucking 3rd world whores without a rubber you’re basically playing Russian roulette in slow motion), and then her cunt went on top of that.

Even with the top down, it was a bit of a pain in the ass fucking in the back seat. She kept her clothes on, I just had my dick out, and the best position was a sitting reverse cowgirl. She rode me until she came (pretty sure this one was real), and then I had her pull the rubber off and finish me, having her swallow it down. As she would learn, it’s almost impossible for me to cum with a rubber on, and I didn’t want to make a mess on the guy’s vintage seat.

I could tell the driver, a young guy, maybe 25, watched from the trees. Good for him, I hope he rubbed one out.

When we got back to the resort, we hung out by the pool until dinner, then went to one of the themed restaurants instead of the buffet. There was music and dancing every night. I don’t dance, but she wanted to, so we compromised. I danced a little, and told her she could dance while I watched, as long as she danced with girls.

Unfortunately, the one thing I could not buy from her was lesbian sex. A shame, really. But dance and even grind on a girl, a few kisses for the camera? Sure, Maria was down for that.

When we got back to the room, it was nearly midnight. She wanted to get into bed. I wanted to get into her ass. If you’re going to do anal in Cuba, bring your own lube, it’s not something you’ll find at the store.

We did it on the balcony. She sucked me to get started, then rolled the rubber on. I bent her over the railing, and fucked her pussy while I massaged her asshole with my thumb, rubbing in the lube I had brought in hopes I would get to use it for more than jerking off. She was so tight, and she had trouble holding in her squeal as I pushed into her. It took a while before she began to enjoy getting fucked in the ass, and I took it slow and gentle. Treating her like a whore was one thing, but sending her screaming with a prolapsed rectum would have ruined my week.

What an experience. The surf was crashing 100 feet away through the trees. The air was warm but a cool breeze blew her hair. I had her bent over the railing, fucking her ass where anyone walking by could see what was going on. She was groaning and grunting, taking it like a good slut. When I was ready to cum, I pulled off the rubber, but she shook her head no when I told her to suck me the rest of the way. So I just jerked off over her face for the second time that day.

If cum is good for the skin, a week with me meant her face was going to be glowing.

After that, it was off to sleep. In the morning, I woke her up with my rubber-clad dick pressing against her. It was almost like “making love”, soft and sensuous, no acrobatics, vigorous but not rough. I finished on her belly. Well, I finished shooting from her pussy, and hit everything from her splendid tits to her neatly trimmed cunt.

For six more days, this cycle repeated. It was paradise. Fucking her sexy ass daily, banging that tight pussy several times a day, getting my dick sucked whenever I wanted. Drinking and smoking cigars and just relaxing together in between.

If you want, these girls will connect with you on social media. They’ll try and milk you for gifts in between trips, but the main goal is to ensure they know in advance when you’re coming down, so they are free. And to let you know what to bring with you, since things we take for granted, like aspirin, often are impossible to buy down there, and other things, like soap, are often rationed. I played along like I would keep in touch, but I didn’t. Each trip is a different resort, and a different girl.

But I have to say, Mary was the best piece of Cuban ass I have ever had.