Meeting Gregorio Fuentes for the first time was a profound and awe-inspiring experience. At the age of 97, he stood as a living testament to a bygone era, a living connection to the legendary writer Ernest Hemingway.

When we arrived at the La Terraza, Gregorio was sitting near an open window eating a plate of scrambled eggs and toast. He was wearing a baseball cap appropriately inscribed with “Captain” across the front. At first glance, he looked exactly the way I had envisioned him.

His face and hands were etched with the intricate lines of time, a testament to a life at sea and the challenges faced on the open waters. He offered his wrinkled, sun-blotched hand and surprisingly, when he squeezed the strength of his grip confirmed he was a man who spent his life laboring on the vast blue ocean.

“The old man was thin and gaunt with deep wrinkles in the back of his neck,” Hemingway wrote in the opening passage of “The Old Man and the Sea.” “The blotches ran well down the sides of his face and his hands had deep-creased scars from handling heavy fish on the cords. But none of these scars were fresh. They were as old as erosions in a fishless desert.”

I was apologetic about interrupting his lunch.

“Senor Fuentes, Daniel,” I said. “Siento molestarte.”

“No, no” Gregorio said. “No problema.”

I pointed to the bar and motioned that I would return to his table when he was finished with lunch. I joined the boys at the bar and ordered a Cubata and an Añejo double for George.  Harry was already drinking a can of lemon-lime pop through a straw.

Just as I ordered a second round, a middle-aged man sauntered through the saloon doors and introduced himself as Rafael, the grandson of Gregorio. He spoke a little English but George was there to interpret for me.

He was curious about our interest in his grandfather and I was sure he’d try to monetize our little chic-chat if he could. I explained I was just a regular schmoe who happened to be a huge Hemingway fan.  When I heard the Captain of Pilar was still alive, I had to meet him in person. Rafael ordered a Chrystal and sat on the stool beside me.

When Gregorio waved, Rafael directed us into the spacious, main dining room for our conversation with his grandfather. We sat down at a long table with Gregorio at the head. I gave the old man a Romeo y Julieta Churchill cigar in the tube. He thanked me then carefully cut the label off the cigar with a small pocket knife and lit it.

Through the large open window came a salty breeze with the scent of the sea. We could see the picturesque bay where Hemingway kept “Pilar” moored for over two decades.  Now there are only small wooden skiffs of various colors and designs swaying to the gentle rhythm of the tide. The ambiance of this experience will be with me forever.

On the walls of the dining room surrounding us hung framed photographs of Gregorio together with Papa Hemingway. In one photo Gregorio is sitting in the pilot’s seat of Pilar as Mr. Hemingway and a friend are hoisting a giant Marlin onto the boat deck. Another image shows Gregorio and Papa on the pier weighing several marlins for the camera. (Photo)

I fed George questions he addressed to Fuentes. Through a plume of cigar smoke, Gregorio began by telling us he was born in the Canary Islands and came to Cuba when he was just a small boy. His father was killed on the passage over when the ship’s mast was torn loose in a storm and crushed him to death. When Gregorio arrived in Cuba, he was adopted by a local fisherman and raised in Cojimar.

Gregorio met Hemingway for the first time at sea. One afternoon in the early 1930s, Hemingway had been fishing the Gulf near Dry Tortugas when his engine gave out. Gregorio was on his way to Key West when his keen eyes caught a glimpse of a small fishing vessel bobbing helplessly in the distance. Without hesitation, he altered his course and guided his boat toward a man waving for assistance.

The stocky man sighed in relief when Gregorio pulled up alongside him and boarded Fuentes’s boat. They shared wine with bread and onions and he said Hemingway was thrilled to have it. He fondly remembered Hemingway commenting on the tidiness of Fuentes’s boat. Gregorio brought Hemingway to Dry Tortugas where he found a mechanic to repair his borrowed craft. Hemingway said prophetically, “If I ever own a fishing boat, I’d like you to be its Captain.

In 1934, with the royalties he received from a movie deal based on his novel, Hemingway was able to purchase his custom-built fishing yacht.  Constructed in Brooklyn, New York, Hemingway had it shipped to Key West. He christened it “Pilar” after the Patroness of Aragon, a city in Spain.

Several years later Hemingway moved to Cuba and bought a home on a hillside in San Francisco de Paula called Finca Vijía (Lookout Farm). Pilar was moved there permanently. True to his word, Gregorio was hired as Pilar’s first mate. He remained with Pilar until the writer died in 1961.

As we sat and listened, Fuentes’s stories painted vivid pictures of his adventures with the American writer. Gregorio piloted the “who’s who” of mid-century American culture throughout the Gulf Stream on Pilar.  Guests included Hollywood royalty like Gary Cooper, Errol Flynn, Ingrid Bergman and others.

When Hollywood came to Cojimar to produce the movie version of “The Old Man and the Sea” they needed a giant Marlin for the scene where the Old Man (Spencer Tracy) catches the giant fish. Unsuccessful at catching one in the Gulf Stream, Hemingway, Fuentes, and a small film crew traveled to Peru where they caught a record-breaking 850-pound black marlin that was used in the movie.

I asked Gregorio an important question. I was curious to know how long he continued to fish after Hemingway died. His answer shocked everyone at the table and in some small way, changed my life. He answered that he never fished again after Hemingway died in 1961. “I could never be as close with anyone as I was with Mr. Hemingway,” Fuentes said.

The last time Fuentes saw the writer was a year before he died when he was standing in the doorway of his home. He told Gregorio he had to leave Cuba because Fidel didn’t want him here, but it wasn’t true. The writer was having a mental breakdown and would never return to Cuba again. He killed himself in Ketchum Idaho the following year.

Pilar is dry-docked today at Hemingway’s home in San Franciso de Paula, twelve miles from Central Havana.

Now part of the Hemingway Museum and open to the public. Although Hemingway bequeathed “Pilar” to Fuentes, it’s unclear whether he donated the boat or if the government confiscated it.

Gregorio was incredibly lucid for a man 97 years old. Before we parted, he graciously signed my hardback edition of “The Old Man and the Sea.” I tucked forty bucks into his shirt pocket and told Rafael it was for cigars.

When we left La Terazza, I turned and waved goodbye to the Old Man, but I knew I knew we would meet again. Driving out of the village, I tried to imagine what it looked like in the 1950s. I’m sure Hemingway would still recognize it today. Nothing has changed.  The car was quiet as we drove to our favorite watering hole in Old Havana.

Riding along the Malecon, George pointed to a building and said it was where he met Che Guevara for the first time. I was taken aback that George had met Comandante Guevara in person. Che was killed in 1967 but remained a national hero in Cuba and a symbol of revolution around the world.

Assessing whether Che Guevara was a “good man” is subjective and depends on one’s perspective. I knew that Che Guevara was an Argentine doctor-turned-Marxist revolutionary and that he played a significant role in the Cuban Revolution. Supporters often view him as a symbol of anti-imperialism, social justice, and the fight against oppression. I knew he even sacrificed his life for the cause of revolution and to promote equitable societies.

In the 1950s, Ernesto “Che” Guevara was introduced to Fidel and Raul in Mexico, a meeting that would shape history. Drawn together by a shared goal of overthrowing oppressive regimes, they forged a revolutionary alliance.

Che was captivated by Castro’s charisma and unwavering commitment to social justice. Inspired by the struggle against imperialism and poverty, Guevara joined forces with Castro to launch the Cuban Revolution. Motivated by a fervent belief in the power of the people to effect change, Guevara dedicated himself to Fidel and the Castro revolution, eventually becoming a global symbol in the fight against oppression.

On November 26, 1956, Fidel, Raul, Che, and seventy-nine believers, sailed from Mexico to Cuba on the Granma to set in motion the revolution that would eventually overthrow the US puppet dictator Fulgencio Batista.  It took three arduous years of guerrilla warfare. Fighting out of the Sierra Maestra mountains in southern Cuba, Castro’s radio broadcasts across the island helped him eventually gain enough support from the Cuban population to end the reign of Batista.

I asked George to tell us the story about meeting Che face-to-face.

“I’m telling ya straight, Chico,” George said. “This ain’t no bullshit.

“At the beginning of the revolution and shit through most of the 1960s the people was expected to volunteer for projects around Havana,” George said.

“So I show up on a Sunday morning at a construction site to help prepare it for the workers that come the next morning. We were stacking bricks and boards around the property so when the crew arrive they could go straight to work. Everything would be ready for them,” George continued.

“Around noon, a military jeep pulls up in front with a driver and someone in the passenger seat. Who jumps out but Che Guevara and everyone stopped. He said he had come to volunteer with us. The first thing he do was grab a wheelbarrow and started loading it with bricks and wheeling it around the yard.”

“Now I have seen a lot of motherfuckin’ pictures of the Castro brothers posing with a machete in their hand in the middle of a sugar cane field,” George said. “But it was just to get the people happy to work hard for the revolution, but I know it was all bullshit. So I figured Che come by to pose for some pictures and give us a speech”

“But what happened that day I’ll never forget,” George said.

“That son-of-a-bitch just put his head down and start working like a motherfucker and work harder than any of the damn volunteers. He took his shirt off and tied it around his waist and just kept going”.

“At first, everyone wanted to work alongside him but couldn’t keep up. One by one they started falling off. One motherfucker needed to piss and another one pulled out for a drink of water. But Che, he kept working like a son-of-a-bitch.”

“After maybe three hours, he put his shirt on and called everyone to the front. He stood there and told everybody he was leaving. He said ‘I’m not leaving because I’m tired, I’m leaving for another work project somewhere else.’ He thanked everyone for their effort and support of the revolution.”

“Then he took three steps, gave that Russian salute, clicked his heels together, and said ‘Hasta la Victoria Siempre!’ (Until Vistory Forever). He turned and climbed into his jeep and left. From that moment on, I knew Che Guevara was the real deal.”

As George was finishing the story we rolled up in front of Castillo Farnes. We sat on a sidewalk table so we could get a closer look at the girls circling us like hungry sharks. I spotted two young ladies across the street and gave them the high sign. The next thing we know, they’re sitting at our table.

One of the girls was a tall morena and the other was a pretty white girl with beautiful brown eyes and long brown hair. The black girl said her name was Yudi and her friend was Lisette. I did my best to make conversation with Yudi.

“No comprendo inglés,” Yudi said.

“Tu Pais?”

“United States,” I said.

“Estados Unidos?” Yudi said with a surprised look on her face. “Miami?”

“No todo Americanos viven en Miami,” I said smiling.

“Cubanos Si”

 Harry was already locked to Lisette so it looked like Yudi was with me. She seemed nice, had a cute smile, nice tits and was overall very attractive. She had a coffee-colored completion with a touch of cream and straight black hair to the middle of her back.

Jinetera’s always want to know two things right away. The first question is where you’re from and the second is whether or not you’re staying in a hotel.

“Estás en un hotel?” Yudi asked.

“No, I’m in a casa particular,” I said. Yudi smiled.

These Cuban broads have the whole thing figured out in milliseconds. They know they’re coming home with you and they know hotels are a hassle which meant,  so far everything was looking good for them.

When you first start experiencing the jinetera culture, you believe you’re scoring big when you get a girl to stay the night for $20. Later you realize you’ve been played.  They’ll scam some pocket change out of you, a Cubano sandwich, a few drinks. You’ve been manipulated and controlled the whole time. Cuban women were very clever. It’s about survival.

I liked having George around to interpret for me but I had to be careful with this slick fuck as well. I’m not sure he always translates exactly what I tell him. He’s put me in a “trick bag” a few times. But I realize I’m the mark, the “Yuma.”  Yuma’s are foreigners and the only ones with any money in their pocket. When you’re having so much fun, you just let it slide.

We were getting ready to leave and I realized I hadn’t eaten all day so we all went next door to Bar Monserrate where I of course, the “Yuma,” treated everyone to a meal. Bar Monserrate was a good place to hang out, especially at night. They usually had a live band and the food was better than average.

When we left Monsuratte, George decided to stay in Old Havana and look for tourists. I thought about taking both girls back to my place but I knew the more I drank, the harder it would be to keep an eye on both girls. I didn’t want to wake up alone, in the middle of the night with my money gone. It happens all the time. I checked Yudi’s carnet (ID card) to verify she had given me her real name and made sure she lived in Havana.

I’ve heard “whore” stories about girls who come to Havana from the provinces and pick up tourists. They give their mark all false information including names and addresses. They might slip him a “roofie” or something and take all of the guy’s money and disappear back to some backwater town in the hills or Oriente. The next day he doesn’t remember anything.

If I said Yudi was a “good girl,” it would mean something different thing in each culture. If she comes home with you, you assume she’s a hooker. In Cuba today, the line is blurred. You may be going home with a lawyer, a doctor, a teacher, or an agent for state security. You never know.

From the girls’ point of view, If they can be taken out to a nice dinner, go to a club for music and drinks, sleep in an air-conditioned room in a modern casa particular, have sex all night, and be treated to a delicious breakfast the next morning, why not? And…. you’ll give them money and maybe a gift on top of it? Their alternative is going home to an overcrowded house, eating black beans and rice, and sweating all night in a hot box with no aircon. No thanks!

Yudi was a genuinely sweet person and worked full-time as an elementary school teacher. The evening evolved into a kind of romantic date night of holding hands and soft kisses. Usually, my evenings dissolve into a blurry, drunken kaleidoscope of tits and ass. This was something different.

If a girl fucks you, she’s expecting at least $20. Sometimes I can barter with underwear, soap, or perfume. But to put things in perspective, if I found a hot-looking girl in the States, twenty years my junior, and took her out for dinner and a night on the town, it would cost me at least $200. And there is no guarantee of a kiss goodnight. If I wanted to buy sex, especially in places like Las Vegas, it’s a cool $2000.

It was getting late so I offered Yudi money for a taxi but she didn’t want to go, so I let her stay the night. I woke up the next morning to the sound of the shower running and turned over to wait for her. When she came out of the bathroom, she was fully dressed so I thought okay, no sex. We had a nice evening, no big deal. I thought I’d walk her up to 5^th Avenue and have a drink while she flagged a taxi.

We sat outside Pepe’s place and had a couple of Cristal’s and an order of French fries. I enjoyed her company so I handed her 20 dollars and a fin for the cab. Girls will always ask you for ten bucks for the taxi and it usually works on stupid tourists. The girls take the money and catch a gooney government cab for a buck or flag someone down and get home for free.

Yudi pointed to her finger and asked me if I was married. When I told her I had never been married she gave me kind of a surprised look and whispered, “Por que?”  It’s funny, I didn’t have an answer for her. Over the years I’ve been in long-term relationships that I thought might last forever, but I’m not a forever kind of guy.

Then the craziest thing happened. I was thinking about the first girl I ever loved and it took me back to my early teens to a girl named Kathy. We met as kids and later worked together in a grocery store in Cleveland. We ended up dating for a few months but sometimes when you want something too much, it slips away from you.

I didn’t know how to explain why the relationship ended so I told her we were planning to get married but Kathy was killed in an automobile accident. Just thinking about that scenario put tears in my eyes and they began rolling down my face.

Yudi sat there mesmerized by my story and had tears in her eyes as well. We sat there in silence for the next ten minutes as we nibbled on the fries and drank another beer.  I went inside and paid the bill and Yudi was standing beside the table when I returned. I started to hug her and say goodbye when she said that she needed to come back to my house with me, she left something in the room.

As we approached the house Laura was sitting in a rocking chair on her front patio with her youngest son Samuel.  Laura just smiled and gave a cordial wave as we walked by her and into my private side door entrance. What happened next inside my tiny room was one of the most intense sexual experiences of my life.

The post Chapter Twelve appeared first on The Cigar Diary.

With another successful venture under my belt, I called Rick Munday, head of VIP Services at the Las Vegas Hilton. He was reluctant to go into detail over the phone but confirmed he was in the market for Cuban cigars. He suggested I reach out when I had a larger supply available.

The cigar boom was booming and the demand in LA was increasing exponentially. Now that Hollywood stars like Arnold and Sly were featured on the cover of Cigar Aficionado, everyone wanted to be part of the new fad. I had celebrity contacts in the film industry who smoked so now I needed to increase my supply to a minimum of 25 boxes per month.

My travel itinerary was getting stale so I rerouted through Mexico City for a change of pace. The downside was flying via Mexico City was it required a red-eye flight out of LA.  I’d arrive in Mexico around 6:00 am and the connecting flight to Havana didn’t depart until mid-morning. Before I knew it, I was back on the road again.

I arrived at LAX around nine and checked in. There was a nice bar across from my gate where I had a couple of Vodka Martinis and a few tall IPAs. I thought the booze would help me sleep on the overnight flight but I was wrong. I even took a sleeping pill to ensure some rest but to no avail. By the time I arrived in Mexico City at five in the morning, I was a fucking zombie.

Now I had to deal with a four-hour layover. After clearing through immigration and customs, I went to Baron Rojo Restaurant and ordered some breakfast. After some lousy pancakes, burnt bacon and coffee, I staggered to my gate and crashed in a chair until it was time to check-in.

Every minute of the layover was painful. I felt that I was near death. But somehow, some way, I made it through again. At nine, I got in line with mostly Mexican and Cuban passengers carrying large bags, giant boxes and silly Western hats stacked five high on their heads and checked in for Havana.

Three hours later I walked out of Jose Marti International Airport and into the suffocating July heat.  Harry was there to pick me up. He had found a new apartment for me in the Miramar district called Reparto Nauticol. Once a gated community for the wealthy, Nauticol was now a residential neighborhood for government employees and Fidelista’s to reside. According to Harry, even Fidel’s son, Alejandro, lived on the next street.

Nauticol was only a block from the ocean and I was also moving onto the same street as my boxing idol and new acquaintance Teofilo Stevenson. My new place was an upstairs studio apartment owned by a large middle-aged divorcee named Teressa who lived next door with her teenage son Alejandro.

We dropped off my bags off and went for egg rolls and fried rice in Barrio Chino. After a mojito stop at Café de Farnes, we rolled to Old Havana and picked up Dolce Maria. She was such a sweet little girl, I enjoyed banging around with her. Short and petite, she had thick brunette hair and large brown eyes and a very hairy pussy which I found kinky. I didn’t mind spending a few extra dollars on her.

Being with Dolce Maria was almost like a real boyfriend/girlfriend experience. At night we’d strolled down to the water hand in hand and sit on the break wall of a large rock that was dumped in the water from a nearby construction site. With the sound of the black waves stirring around us, we’d lay there looking up at the twinkling night sky.

One night, lying there I made the decision to become a writer.  Dolce Maria asked me what I wanted to do with my life and told her write. The night sky is extremely clear from the Caribbean. I pointed up to the brightest constellation above us and told her I would take its name as my “nom de plume”…it was Orion’s belt.

Maria smiled and whispered, “Daniel Orion.”

Later that night we had a few Cuba Libre’s and watched a Latin soap opera for an hour or so and went to bed. We fell fast asleep without fucking but horny little Dolce Maria woke me up in the middle of the night. Laying like two spoons in a drawer, she moved close and started rubbing her little ass against my dick.

 Although I was half-asleep and half-drunk, I was hard in five seconds. As I was climbing on top of her, she spread her legs wide to receive me and we started pounding away.  Little Maria must have been dreaming about sex because she started thrusting her hips up and down to create a rhythm. Our passionate lovemaking transported me to another world. It was one of the best fucking experiences I ever had.

The next morning when I came out of the shower, Maria was sitting topless, her back against the headboard. She asked me about a bottle of Smirnoff Vodka I had sitting on the mini-fridge. She wanted to give it to her father as a gift. “Si,” I said. “no problema. Un regalo para tu papa.”  She motioned for me to throw the bottle so I grabbed it off the fridge and tossed it over to her.

I threw it too high and the bottle bounced on the bed and then I heard a dull clunk sound. Suddenly she had her head in her lap and was holding her mouth. When she removed her hand, her front tooth had been knocked out. Oh my God…. now what? The tooth had been broken off at the gum. I could see the root dangling in the center.

I called Harry and told him we had to get Dolce to a dentist immediately. The wait time for a dentist in Cuba was weeks if not months so we had to take her to a hospital used by tourists called Clínicia Cira Central Garcia in Miramar. I could pay cash there and get her treated immediately.

We arrived at the hospital we had a dentist assigned to us within 15 minutes. He and his assistant performed a root canal on Dolce Maria to eliminate the pain. The whole procedure only took about 30 minutes and cost me $100.

We made an appointment for the following week to see about getting her a dental implant but when we got to Dolce Maria’s house her father said she had gone to the beach with friends. Cuba never ceases to amaze me. Oh well, apparently hustling money day was more important than having a front tooth.

I found a new cigar supplier named Ray who lived downtown on Obispo Street. Obispo Street is in the heart of old Havana and it’s one of the main drags that cuts through the city. This famous old Calle was constructed in the 1500s.  It’s a crowded, narrow walking street lined on both sides with stores and restaurants.

At one end of Obispo is the El Floridita Restaurant/Bar the opposite end of the street is Hotel Ambos Mundos where Ernest Hemingway resided in the 1930s. His room on the fifth floor is now a museum. Hemingway had a home in Key West at the time but moved to Havana permanently in 1940 when his third wife Martha Gellhorn found a home in San Francisco de Paula

Ray was a great guy and had a striking resemblance to Hollywood actor Armand Assante. He charged $25 per box and offered to extend credit if I didn’t have enough cash. It takes him a few days to find the boxes together so I have to order them as soon as I arrive and pick them up the day before I leave. I think his black-market (La Bolsa Negra) cigars are rolled in homes or possibly stolen from the factories, but the samples he showed me looked great.

With Dolce Maria MIA, I decided to hook up with Melanis. She was a nice Mulatta girl, a little low-key for me but I knew I could trust her.  Melanis was always glad to see me and told me that her sister Yoani had someone she wanted me to meet.  It turns out it was Yoani’s boyfriend William, a Canadian guy in his 60s who lived on a cabin cruiser in Marina Hemingway.

William was constantly going back and forth between Key West and Havana bringing televisions, microwaves, electronic equipment, and anything else he could sell in Havana.  Yoani thought that he might be able to help me transport my cigars to the States. It was a great idea depending on the parameters of the deal. I wanted a sit-down with William.

Yoani arranged a meeting for the next day and we met on William’s yacht in the Marina. I pitched him on the idea of muling cigars to Key West for me.  This way I could bypass Customs in Cuba and Mexico and rendezvous with him in the US. If he could bring 25-50 boxes to Florida, I’d return to Los Angeles on a train. This would solve my numbers problem. From Orlando, I’d go straight to my VP friend at the Las Vegas Hilton. I could probably unload 30 boxes at the Hilton alone.

When doing business with Vegas casinos, price was no object. ­William had never thought about cigar smuggling but when I explained the profit margins, he was in. It was a win-win situation. Now he could make money going both ways. Our plan was to take 50 boxes each and he would find someone to fence his in Florida.

The first thing I had to do was convince Ray to front me as many boxes as he could. I could buy 25 boxes and maybe persuade Ray and Juan Carlos to spot me 25 each. William wanted  $100 per box to transport them to Key West. He would allow me to defer payment until they were sold. William kept his car in a Key West marina so he could drive me up to Orlando, then the Sunset Limited all the way home.

It took about 10 days to get the order together. Convincing a Cuban to defer payment is harder than meeting Fidel Castro. By the time we were ready to go, Wiliam had 50 boxes and I had 100. The problem we faced was hiding the cigars on the boat. Our solution was to remove the wood paneling from the walls and bury the boxes in the hull, away from the prying eyes of Cuban agents.

At the last minute, I decided to sail to Key West with William. There was too much money at stake now to blindly trust someone I didn’t know very well.  My only concern was clearing Customs at Key West. William laughed when I asked him about it.

“Do you think we’ll be okay clearing US Customs in Key West OK?”

“We’re not clearing any Customs in the US Danny,” William said.

“We’re  going to expand our route and come into the US further East as if we were returning from the Bahamas, not Cuba.”

“Sounds good to me,” I said.

The last night I stayed at Manny’s so I’d be able to grab an early taxi from the hotel. As promised, I met with William at his boat at 5 AM. He was sitting in the cabin drinking coffee when I arrived. He had sandwiches and cokes ready for the agents who would be Inspecting the boat.

The first group to arrive was immigration. They took our passports and visas to their office. A few minutes later Customs boarded and last but not least the damn Cuban Navy even came aboard. They probably just wanted a free sandwich and drink.

They were extremely cautious with cabin cruisers leaving Cuba. A large boat was a perfect way to traffic Cubans out of the country. Most Cubans had rich relatives living in Miami who were willing to pay up to $10,000 to get a loved one out of this shithole. It was a lot safer muling cigars than people, but if we’re popped, they’ll probably confiscate William’s boat and boot us both out of the country.

William knew a few of the government agents considering he travels in and out of Havana so often. The boys ate their sandwiches and drank their cokes before nonchalantly snooping around the cabin and engine room below. The whole process took less than an hour.

Once we were cleared and our passports returned, William kicked up the engines and navigated us out of the harbor and into the deep blue sea where the Atlantic and Caribbean collide. As we churned across the whitecaps, light was breaking on the horizon. The morning air was warm but the humidity had not yet risen.

I took a moment to reflect on my latest adventure and truly believed it would work out right. As we pulled out of the harbor, William set his barring to NNE 20.58°. The estimated travel time would be around 8 hours which kind of surprised me.

From the deck, the warm salty breeze caressed my face as I watched the horizon slowly transform itself from a deep purple to a swirl of amber-orange and azure blue. The sea reflecting the changing sky mirroring the brilliant colors that danced on the water’s surface. As Havana faded away, the boat left a gentle, rippling trail in the water.

William piloted from the flybridge on top of the boat. I asked him if he could just put the boats navigation on autopilot but he was an experienced sailor. He explained that fact that we were traversing the Straits of Florida which is a busy shipping lane and a collision with a tanker is a real possibility.

I spent most of the journey in the cabin, out of the blinding July sun. The boat’s constant bouncing and pitching started to make me nauseous which apparently was normal. William suggested I focus on the horizon but lying on the cabin bunk made the dizziness go away.

Two hours into our journey, William called me to the flybridge.

“You’re doing good, Danny,” William yelled. “Everyone who sails across with me has thrown up over the rail by now. So, you’re doing good man. Take a look in the distance.”

A couple miles east of our course, a massive container ship was cutting through the shipping lane which was directly in front of us.

“That’s why you have to stay alert Danny,” William said

“If you run on autopilot and fall asleep, you could lose your life.

Approximately seven hours after we departed Cuba, we chugged into a small marina in the Florida Keys. Once we were settled, we dismantled the walls of the cabin and removed the stash from the walls. Almost immediately, I noticed a problem. William had put the cigars in plastic grocery bags that were not sealed air-tight.”

I noticed moisture on the inside of some of the bags. If that salty seawater seeps inside the cigar boxes they’ll be ruined. We could inspect the product closer once we made it to a hotel room in Ft. Lauderdale. We finished unloading the cabin, washed down the boat, and pulled out of town.

As we drove the seven-mile bridge, I crunched the numbers in my head. I had 100 boxes in my possession. The resale value at $300 per box was $30,000. William was owed $10,000. My cigar guys were owed $2,500 then my profit would be $12,500. In Vegas, I could bump up the prices to cover my travel expenses. After a good night’s sleep in a cheap Lauderdale motel, William drove me to Orlando Station to catch the Sunset Limited.

I boarded the train for my two-day journey through the southern states of the country. It would make stops in New Orleans, San Antonio, Phoenix and Tucson. After a pit stop in Las Vegas, it was on to Los Angeles. I booked a first-class Roomette on the lower level which allowed me some privacy. It had two comfortable seats that transformed into upper and lower bunks at night.

I stacked the boxes on the top bunk and wrote “FILM ELEMENTS” on them in case anyone inquired about their contents. I stayed to myself most of the time and had my meals delivered to my room. The only time I left my space was for the bathroom, shower and occasionally a walk to the Bar Car for a cocktail. As we rolled across the wide open country $12,500 kept dancing in my head. Vegas or Bust!

The post Chapter Ten appeared first on The Cigar Diary.

My client list was growing and I needed more product. Getting cigars out of Cuba was the problem. There was a $1000 limit on the total amount of cigars you could take out of the country. I guess I could purchase a few boxes in the Duty-Free store after clearing customs but retail prices were crazy expensive. Another solution would be to bring a travel companion from LA but the upfront costs would double.

I finally made it back to Havana in late spring and Enrique, who preferred to be called “Harry,” was there to greet me. When I arrived at Manny’s I was taken aback when I found my room occupied again but this time his guest wasn’t checking out until the following day. Manny was willing to inconvenience me again rather than lose a day’s rent.  It’s a recurring theme in Cuba.  Greed always “Kills the Golden Goose.”

It’s whatever they can get today and to hell with tomorrow. But maybe it was a blessing in disguise. I asked Harry to find me another casa particular. He said his friend Ronny had a private house in Miramar I could have for $25 a day. It sounded perfect so I told Manny I’d be at another location for a few days and we left.

Casa Ronny was in a small apartment complex but his place was fully furnished and very private. I was alone there with no interference from family or the prying eyes of neighbors. Every time you entered or exited Manny’s building all of the neighbors were watching. If they see anything suspicious, they are expected to report it to the local CDR. (Committees for the Defense of the Revolution).

It took me a couple of days to get acclimated to my new digs. I was glad Harry had a car because the area was mostly residential and there were no bars or restaurants within walking distance. On the corner of 42 y 45, the locals sold espresso and “chicharrones” in the morning along with some pastries. It usually held me over until Harry arrived.

One morning I woke to the sound of pouring rain. I opened my front door and low and behold there was a cute young girl with shoulder-length brown hair sweeping rain into a drain.  Her soaking wet, see-through blouse revealed pert little titties with quarter-sized areolas. I stood there transfixed staring at this beautiful young woman in the courtyard.

I waved her over and she shyly stood in front of me holding her broom with the loud rush of falling rain surrounding us. I smiled and said “como se llama.” “Ida,” she replies with an affectionate smile.  I asked her if she liked ice cream. Te gusta helado?”

“Si,” she replied.

“Vamos!, tu y yo con Enrique en treinta minutos.” I said. She laughed and said “Si” to the total stranger standing in front of her. Another surreal experience was about to unfold.

Harry returned as scheduled and parked in front of the house. When he beeped his horn, Ida bounded out of her house shaking her little ass and gave me a wave. She jumped in the backseat of Harry’s car and we were off to Bim-Bom ice cream parlor on 5^th Avenue. I couldn’t take my eyes off this sweet little piece of ass.

Harry and I ordered chocolate cones and little Ida ordered a hot fudge sundae with nuts.  Watching her eat it was a treat in itself. She had whipped cream on her upper lip several times and several times I tried to lick it off but she shyly pulled away. Harry had known Ida since she was a little girl and agreed she developed into a beautiful young lady.

When we finished our little ice cream charade, Harry dropped us back at the apartment. As we were walking through the yard, I asked Ida if she’d like to visit my house later and she nodded yes.  Sure enough, later that day there was a soft knock on my door and little Ida was standing there barefoot, in a tight tee shirt and short jean skirt.

I turned on the TV and we nervously watched an early evening Spanish soap opera. Well, she was watching TV and I was watching her. Not able to communicate, I thought, what the fuck and took her by the hand and walked her into the bedroom. I took off my clothes and climbed into bed.

Without missing a beat, Ida went into the bathroom and a few minutes later emerged wearing only a towel wrapped around her petite frame.  She laid down next to me and with a coy smile reached out her hand. I tugged softly on the towel and it opened like the blossoming petals of a spring flower.

We gently kissed and as expected, her lips were velvety soft. I tried not to rush the moment but I couldn’t wait to get my tongue between her milky thighs. When I licked her nipple and it stood erect. I trapped it between my teeth and held it there as I flicked my tongue over the blood-red tip. As her eyes slowly closed, I gently kissed her soft tummy and followed a thin line of dark hair that ran below her waist.

I rolled over and opened her legs. I wrapped my left arm around her right thigh and with my left finger and right thumb I opened the gates of heaven. Her swollen clit was exposed to the world now and I licked the outer lips of her pussy in an up-and-down motion until she unconsciously, wantonly, spread her legs wider. “Orgasmo?” I whispered.

“No,” Ida whispered back.

“Si Ida, Ahora!” I said.

My long warm tongue squirmed inside her pussy. I trapped her rosy clit between my upper and lower lips and licked it up and down and back and forth as fast as my probing tongue would move. When her hips began to writhe up and down, I knew I had her where I wanted her. I buried my face deeper into her sex and wrapped my arms around her waist so she couldn’t escape the volcanic explosion that was about to follow.

It was the continuous, rhythmic, up-and-down licking on her little pea of pleasure that soon had the little nymph moaning with desire. Her hips started to hump my face, up and down as she held the back of my head with both hands. Faster and faster and then it happened… She arched her back and tried to pull my head inside her pussy as she let out a shriek of delight and filled my mouth with her warm love juice.

She was spent and I felt somehow satisfied although I hadn’t released my sexual tension. All the same, we lay there in silence, her head on my chest. I looked at her lying there, eyes closed and felt a kind of sadness wondering where she would be in a year, or five years. If she would ever get out of this country and experience all that life had to offer.

When she left, I watched her walk across the courtyard and into the front door of her apartment. I knew we would never be together again. I guess she would just become another amazing experience that would be strung together with the other experiences of my life. I had to constantly remind myself I was on fantasy island to do a job and the job had to be done. If I was to survive myself, I had to streamline this business and maximize the opportunity at hand. I had to control whatever was in my power and not worry about things that weren’t like politics.

Tensions between Havana and Washington were heating up after an international incident earlier in the year. Cuban fighter jets shot down two US airplanes over Cuban territory. They were private pilots flying for the Miami-based dissident group, “Brothers to the Rescue.” They were conducting missions dropping anti-Castro leaflets over Havana. They had made several previous trips violating Cuban airspace until they were finally intercepted.

A third plane in the group managed to escape into US territory. The Cubans in my circle didn’t seem to care. Most hadn’t even heard about the incident. They were focused on survival, not international affairs. Cubans get all of their news from state-run media so they only hear what Castro wants them to hear.

Yeah, Cubans are being fucked again by the United States,” Harry said.  “Clinton signed the Helms-Burton Act which tightened the U.S. Embargo.” This came several weeks after the “Brothers to the Rescue” incident. The Helms-Burton even penalizes foreign entities doing business with Cuba.

There were even some U.S. allies denouncing the Helms-Burton Act as a violation of human rights. But the United States does whatever it wants. The US embargo was put in place by the Kennedy administration and will only be lifted if Fidel Castro and his brother Raul step down from power and Cuba moves toward free elections. Meanwhile, the Cuban people continue to suffer, not the Cuban government.

Brains storming with Harry on viable alternatives to getting product out of Cuba, I came up with a great idea. On my first trip to Cuba, I sent two boxes of cigars by DHL to Ernestina, my travel agent in Tijuana. A week later I drove down to TJ and picked them up. I figured why not ship my boxes to Tijuana and bypass Cuban and Mexican Customs? Then I could drive them over the US border at Tijuana.

The following day, I had George pick up five large shipping boxes from DHL. I spent the day packing 25 boxes of cigars I got from Juan Carlos. George and I took a taxi to the DHL office in Miramar. On the shipping forms, I printed “libros” (books) as the contents. It only cost me $100 to ship the five boxes, but of course, it never goes according to plan.

The following morning, I got a phone call from the United States. It’s my brother James calling from Los Angeles to tell me I had received a call from the Customs Agency in Mexico City. They left a message that they have 25 boxes of Cuban cigars held at their office at Mexico City Airport. To retrieve the boxes, I would have to pay the Mexican import taxes. Now I’m fucked!

Some of those boxes were prepaid by clients and now have to either refund them or make it good on my next trip. There is only one thing to do.  The cost of returning to L.A. and coming back will make this venture a wash so my only choice is to ask James to wire me the money to fill my order and return with the stash.

Now I have added risk and a lot more pressure. I have to return successfully with everything plus a few added boxes to make up for the Mexico City loss. James already has skin in the game so he reluctantly agreed to send me $800 via DHL. They are the only international shipper that works with Cuba. I’d have to wait a few days with the few dollars I had left. How was I going to get out of this one?

George and I went to Barrio Chino (Chinatown) to think this over. We had dinner at Dos Dragones, a joint that’s been around since the 40s. Authentic Chinese food from one of the last great Chinatown restaurants. We started with the best oyster cocktail in the world. They dump about 12 oysters in a tall glass of tomato juice with a splash of Tabasco. As George likes to say, “It puts lead in your pencil, Chico.”

Out of curiosity, I asked George a question. “Do you remember the Superman show at the Shanghai Theater George?”

“Of course, Danny,” George said. “That’s where I used to take my customers to see the live show.”

“I remember the Superman scene in Godfather II,” I said. “During the scene, Superman appears on stage wearing a large red cape. Just as he pulls the cape open to reveal himself, the camera cuts to the gasping audience. Senator Geary: “I don’t believe it, that thing’s gotta be a fake.” Fredo: “That ain’t no fake. That’s real. That’s why they call him Superman.”

Supposedly, Superman boasted an 18-inch cock. He could place 12 silver dollars on his erect shaft. Each show started with a group striptease, and then one of the girls would be tied to a pole in the center of the stage. For the finale, Superman would come out clad in only in his famous black cape and remove it to the shock and awe of the audience.

A chick would suck him until he was hard and then, to the delight of the audience, he’d fuck the girl tied to the pole. There was audience participation allowed and the show got kinkier from there. George said he used to go backstage and see Superman stroking his dick, trying to get it up.  He told George he used it too much and there was nothing left. In the days before Viagra, you had to rely on amphetamines or coke to stimulate yourself. George had seen it all in Havana’s glory days. C’est la vie!

The next morning, I was awakened from a deep sleep by knocking on my bedroom door. George was a little early but what the fuck…I didn’t want a full night’s sleep anyway. We grabbed a couple of cigars and went out on the balcony to enjoy the sunny morning and watch the street activity below.

It was after 2 p.m. when Malagra came out to tell me I had a delivery at the door. I signed for the DHL envelope and I excitedly told George we were going to the Nacional for a nice lunch. I threw the envelope on the bed and jumped into the shower.Now  I had enough money to finish the cigar deal and enjoy my last few days.

George came in and said, “You better check the envelope, Danny, make sure the money’s there.”

“Sure George,” I assured him. “The envelope is still sealed and I’m sure the money is inside.” To appease him, I opened the envelope.

Inside the DHL envelope was another sealed white business-size envelope with my name scribbled on the front. I ripped open the envelope and there was a sheet of typing paper folded inside that read “In for a penny, in for a pound.” A saying James and I threw back and forth. But there was one problem…NO MONEY!!!

WHAT THE FUCK? The inside envelope was still sealed… how the fuck did they get the money out of the envelope and reseal it? I picked up the phone and called James. “Did you put the money inside?” I asked. “Of course, I put the money inside.” He replied, in an angry tone.

“I thought so,” I said. But there’s no money in the envelope.”

Now I was really in a difficult situation. I had already borrowed several hundred dollars from Manny and I still had an order to fill.  James called back and told me to stay in Havana. He’ll bring the money down personally the following week and check out Havana for himself. I agreed it was the best plan at this point. I survived by borrowing more money from Manny and by the time James arrived, I owed him over $600.

For his first night in Havana, James wanted to stay at the Hotel Nacional and I reserved a room from Manny for the rest of the week. On the morning of James’ arrival, I called my friend Angel and told him I needed some chicks to bring to the airport to greet my brother.  “No problema,” Angel said. He said he could drive me and he’d have some hot chicks that would love to greet James.

Later that day, we drove over to Centro Havana in Angel’s dark blue Russian Moskvitch and parked in front of a tall apartment building.  He said he would be right back and disappeared into the shadow of the entrance. I’m sitting there watching people walk by when suddenly Angel emerges with two girls in tow.

“Estas chicas son buenas?” Angel asks. I couldn’t believe my eyes. This motherfucker is standing there with two identical twin beauties. “WOW. Si, Si. perfecto,” I said excitedly. These two will blow his mind.  I instructed Angel to tell the girls to be ready at six sharp and to be waiting in front of their building.

On game day, Angel met me at a little bar on the Malecón.  We had a couple of beers while we waited to grab the girls. The anticipation was killing me. Twins! I’ve never done twins before.  Shortly before six, we headed over to Centro Havana and pulled up in front of the twin’s building, and beeped the horn.

Angel toots again but the girls are nowhere to be found. I’m thinking, this isn’t good.  Angel and I walk up to their door and the apartment looks dark inside. We knocked on the door a few times but nothing.  Now what the fuck are we going to do?  It’s almost time to head to the airport.

Angel grabs my arm. “No problema! Vamos!  We spin around the corner from the twin’s joint and Angel toots the horn again. I look up at the balcony and two girls are standing there smoking cigarettes. Angel goes up and has a little chat with them and I can see them nodding their heads “yes.”.

When he comes back, he has a smile on his face. “Si,” he says. “Chicas en airporto.” Okay, maybe we can get out of this jam yet. We sat there, smoking our cigars and waited. About fifteen minutes later, two stunning chicas saunter out of the building.  One of them introduces herself as Sara.

We spin around the corner and stop abruptly. Angel bangs his horn again and another petite beauty comes out of a dark hallway.  A little blonde about 5 feet tall. She slips into the back seat with the other two girls and we head to Jose Marti Airport.

We arrived around 7:30. On the tote board it said James’ plane had just landed from Cancun. It would take him a good 45 minutes to get through Immigration and Customs so I go over to the outdoor bar and grab some beers. There were police everywhere, so the girls have to stay in the car.

When James finally came out of the airport, he had to maneuver his way through the usual crowd gathered at the exit door. Angel grabbed his bag and I handed him a shot of Havana Club rum and a beer and he jumped in the backseat with the three hotties. It didn’t take him long to get acclimated. I looked over the seat and he’s deep kissing Sara with his arm behind her neck and down the blouse of the petite little blonde.

Angel had found some ringers. Sara didn’t look Cuban. She said her last name is Simon, so maybe that explains it. Before the revolution, there was a large Jewish population in Havana she may have descended from them. As they all kissed and intertwined in the back seat, we drove through the blacked-out Rancho Boyeros on our way to the Hotel Nacional.

As we passed Manny’s building, George was standing in front. I yelled out the window to meet us across the street to the hotel. He didn’t hesitate. He was high-stepping it and almost got to the front door before we did. George didn’t want to miss out on anything, especially free food or drinks.

James checked into the hotel and before I could invite him to the Gulfo Bar, he was up the elevator with the three girls. How he managed that one is a mystery to me. Cuban girls are not permitted upstairs into guest rooms. Maybe he paid off the elevator operator. Not bad for his first night in Havana.

Israel was working the back bar so I took George and Angel for a nightcap. After a few rounds, Angel and George said goodnight and I walked down the Nacional’s long driveway in the direction of the Monseigneur. I didn’t feel like a taxi ride so I crashed at Manny’s. I lay in bed and watched the ceiling fan turning overhead. The sound of salsa music was wafting through the window from somewhere in the night. After all, this was Havana.

The post Chapter Nine appeared first on The Cigar Diary.

It took about a month to get all the boxes sold and distributed but the customer base was expanding rapidly. Once the word got out that Cuban Cigars were available the pre-orders started rolling in.

I thought I would try a different travel route this time.  I decided to fly direct to Havana from Tijuana Mexico.  I had some friends drive me down to TJ and pick me up when I returned. It’s still as risky as flying. I have to get across the border at TJ taking my chances there at the US Customs checkpoint.

The return trip to Havana turned into one long party day. We started drinking at a bar in Redondo Beach at about one in the afternoon before heading south to the border. San Diego was about a two-hour drive and from there, it’s only 18 miles to Mexico.

Once we crossed into Mexico we made another pit-stop at a cantina on Revolution Blvd. The Tequila shots and Corona’s were flowing like water. After a few greasy tacos and a few Margaritas to wash them down, they dumped me at the airport around 5 p.m. for my 8:30 flight. It was roughly five hours to Havana.

With the time difference, the direct flight landed at Jose Marti around 5 a.m.  I got through immigration and customs rather quickly and took a taxi to Manny’s house. When I pulled up, Manolo was waiting for me on the front steps of his building and helped me carry up my bags.

He told me an American was staying in my room but he was checking out around ten in the morning.

“Let’s go for a beer, Danny,” said Manny.

“Sounds good to me”

We put my bags in Manny’s room and he gave me a Monte number two for the ride.

I grabbed a few bucks and my black beret and exited down the back steps into the garage.  Manny owned a Czech motorcycle with a sidecar. Coolest thing I ever saw. We pushed it outside, gunned it up and I jumped in the car.

It was another “peak experience” as Psychologist Abraham Maslow called it.  We were cruising down the Malecon as the sky was turning from dark to light, casting its first streaks of sunlight across the ocean. With the cool breeze blowing on my face and the waves crashing over the sea wall, it was magical. I was back in Havana.

He took me to the famous Hotel Deauville in Centro Havana off the Malecon. It was built in the casino/hotel boom of the 1950s by American mobster Santo Trafficante, Jr. It was co-venture with President Fulgencio Batista who in the 50’s offered tax incentives to encourage construction and Casino projects in Havana.

The Hotel Riviera, Hotel Capri, Hotel St. John, and the Havana Hilton, all resulted from these government incentives.

The Deauville is just a shell today of what it once was in Havana’s glory days.  We sat in the front lounge and drank several cans of Bucanero.

We went back to Manny’s at about 9:30 as the American gentleman was getting ready to leave. He was a unique-looking individual. About six feet tall, with long blonde hair, and dressed in a commercial pilot’s uniform. I assumed he was a pilot for an American Airlines company but the look didn’t match the profession.

His name was Kirt and he was also from California. He said he was in Havana looking for airplane parts. He claimed he’d be back in a week or two.

“The pussy is amazing here, and cheap,” said Kirt.

Well, he was right about that. As soon as Kirt was gone and room was cleaned, I hit the sack.

The next thing I know someone is knocking on my bedroom door. “Hey, Danny, what d’ya say, Danny?” “It’s noon Danny.”

Jesus Christ! “OK George,” I yelled through the door. “Give me five minutes.” I crawled out of bed, took a quick shower and we walked down to Wakamba for a bowl of spaghetti.  Afterward, we stopped at the Hotel Nacional for a few drinks on the back patio. After the second drink, I told George I’d catch him later and went back to Manny’s for a nap.

Later that evening I went to the Monseigneur cafeteria and had a couple of drinks.  Alfredo was there so we shot the shit for a few minutes then I headed up La Rampa.  I took a slow walk around the block, past the theater and ice cream park, past La Roca restaurant, and back down 21^st Street to Manny’s.

Manny had an authentic Cuban dish of chicken and rice prepared when I got back. After a dish of flan for dessert and an espresso, I went across the street to a little outdoor bar on the side of the Nacional. There were several plastic tables with chairs to sit down. They only served beer so I grabbed a Hatuey and lit a cigar.

I noticed two young girls hitchhiking across the street on the Malecon. One was a dark-haired girl and the other one was a petite blonde wearing powder blue spandex shorts, a black tank top, and flip-flops. They kept staring at me so I gave them a high sign and they started walking in my direction.

As they approached the table I asked them if I could buy them a beer and they both giggled at each other and said “Si.” They pulled out some chairs and sat down. I shook their hands and said, “Daniel.”  The dark-haired girl was Clara and the blonde was Sonya. I went back up to the counter and ordered two more beers.

After a few minutes of struggling to make conversation, a man and woman appear in the distance and begin walking toward us from the Malecon. I saw them earlier, sitting on the break wall about 30 feet down from where the girls were hitchhiking. Maybe they were some kind of a tag team of scammers?

Sensing something was off, I proceeded with caution.  The girls were young and pretty and probably bait for some kind of a tourist trap. The lady walked up and introduced herself as Sonya’s mother and the guy as her friend from the neighborhood. I invited them to join me for a drink. I grabbed a few Cristal’s and sat there trying to communicate without much luck. They seemed a little intimidated talking with an American from California.

I don’t know how old little Sonya was but she was stunning. Her blonde hair fell to the middle of her back and she had beautiful dark chocolate eyes and a perfectly round little ass.  After a few moments of chitchatting, the mother invited me to their house the following evening for dinner so I could get to know their daughter better.

I went up to the counter and grabbed a pen and pencil and had her write down the directions.  After another round of drinks, Mom got up and said hasta mañana.  I hugged Sonya and told her I’d see her the following evening. I couldn’t get that image of the little blonde’s ass in those tight, blue spandex pants out of my head.  Still, in the back of my mind, I sensed something wasn’t right.

Maybe this could be some kind of a setup. The dude that was tagging along looked like a cop and was wearing those black Army boots that Cuban cops wear. Better safe than sorry, I needed to let this one go. There would be another one of Castro’s cuties around the next corner.

The next night I was sitting at the same place when a couple of guys came rolling up on bicycles. They introduced themselves and asked me if I needed anything in broken English. Half kiddingly I said, “Yeah, I need something… a beautiful young girl with really big tits.”  If you can help me out, I would appreciate it.”  They looked at each other nodded their heads assuredly and told me they could bring a girl tomorrow. They asked me to meet them on the corner past the Hotel Capri at 7 pm.

Manolo and I shared one of his famous lobster dinners again with lots of melted butter. Butter was harder to find in Havana than lobsters. On the side, we had white rice and plantains. After dinner, we enjoyed an espresso on the balcony and drank a couple of shots of Havana Club 7-year rum.

Manny legally owned the house that he lived in. It was originally his grandfather’s place. When his grandfather died, his father brought the family in from the country to live in Vedado. His father who worked in the sugar industry was jailed at the beginning of the revolution for being considered a wealthy capitalist.

After Manny finished college at the University of Havana, he bought the deed to the house from the Cuban government so now he owns it free and clear. Because of the location, I think it will be worth a fortune in the future – in post-revolution Cuba. If there ever is a “post-revolution.”

Since it was approximately 7 o’clock, I thought I’d saunter up the street to see if I could spot the bicycle boys. When I reached the Capri, I noticed my jineteros were sitting across the street, and lo and behold, they had a girl sitting betwixt them.

The girl appeared to be a pretty teenager with dark features and really big tits, all wrapped up in a low-cut, full-body red spandex, one-piece bodysuit. HO-LEE-SHIT!

My eyes almost popped out of my head when I got a closer look at the chick.  She was really cute and when she stood, she showed me had an incredible ass to go along with the big tits.  I invited everyone for a drink at a little outdoor restaurant on La Rampa. Her name was Alyeska. She offered to stay with me that night but would need $30 in the morning for her mother. Of course, I agreed.

The boys made their exit and I walked Alyeska back to Manny’s house. We went out on the balcony and she sat on my lap in the rocking chair. It was another romantic experience. Feeling the warmth of her skin against mine, we didn’t try to speak. When our eyes met, a silent conversation ended between us.

Then the gentle, hesitant touch and our lips finally met. A soft delicate kiss, our lips molded to one another, a perfect fit. I walked the young lady into my bedroom.  She showered and climbed into bed naked. I turned off the light and climbed in next to her.

The room wasn’t entirely dark. There was some light filtering through the slates of the window. There was Latin music coming from somewhere in the distance. As Alyeska lay on her back, I reached over and pulled her close, and pulled her head to my chest. It was a way of relaxing her and letting her know that everything would be alright.

I slowly pulled the covers down exposing her large breasts and I slowly began to message them one at a time. Her nipples grew hard when I pinched them and she started to moan when I began to suck them. They stood erect like large studs in the center of large brown areolas.

She had a shy, passive nature, which brought out my domineering side. The more passive she behaved the more domineering I became. I grabbed a handful of her thick, curly hair and held her head against the mattress so she couldn’t move.

I brought my middle finger down and slid it over her pussy. Then I let my fingertip slip between her folds and felt her wetness. She sighed and tried to turn away but she was pinned. Her eyes rolled back into her head.

I parted her with two fingers and found her little wet clit and began rubbing it in small circles. She gave a crying sound as I put my lips against hers to muffle her voice. The taste of her, the smell of her, the feel of her, so close to my skin was unforgettable. She was lost in a sea of pleasure now. There was no turning back now for my little girl.

She started thrusting from side to side but couldn’t break away from her powerful master. She was convulsing against my hand and I was rubbing faster and faster when she released her squirting wet orgasm into my large worker’s hand. She gasped for her breath and then slowly began to relax as her breathing quieted. She lay there, hot and damp from the exertion of her orgasm.

Our lovemaking was completely unselfish. She was spent from my domineering play so I forfeited my moments of pleasure for hers. There would be more nights together. I just wanted to give her a forced orgasm that she wouldn’t forget. If you can make a girl cum like that, you can get away with a lot thereafter. She was mine now.

The following morning, we were awakened by the sound of laughter coming from the adjoining room.  She lay there with a stoic look as I messaged her tits and sucked her nipples.  We took a shower together and went out on the balcony for coffee.  As promised, I gave the busty bitch $30.   I wrote MOMMY on the envelope and folded it into her hand.

My guess is she paid a $10 commission to the bicycle boys for their introduction and brought $20 home to her family. What a night. It was another incredible experience. I had full intentions of exploring this relationship further but didn’t think it would be so soon.

The following morning Alyeska returned to my apartment and brought a cute, young friend named Marta. Her petite little friend had sandy blonde hair and beautiful brown eyes. We sat around my bedroom for a while drinking beers and then I invited them to the pool at the Hotel Nationals. I brought a bikini with me and as luck would have it, it fit Alyeska like a glove, exposing her big breasts and the tops of her beautiful chocolaty brown areolas.

Marta was satisfied wearing shorts to the pool.  The security guard stopped us at the entrance and started berating me about bringing teen girls to the family-friendly pool. After a minute or two of this guy’s bullshit, I looked at the girls and said “Vamos.” We walked up LA Rampa to the Habana Libre pool on the second floor.

Besides the lifeguard, we were the only ones there. We frolicked around for a while and played some tag. When Alyeska rode on my shoulders around the pool, her tits kept falling out of her bikini top.  The lifeguard didn’t seem to mind.

As the afternoon began to fade away, they had a poolside lunch of Cubano Sandwiches and cokes while I downed a few Cuba Libres’.  Since the hotel was close to Centro Habana, we said our goodbyes in the front lobby. They went one way and I went the other.

That evening George showed up with a plastic bottle of “gooney” rum.  It’s the rum that’s made specifically for sale in Cuban peso stores and not for retail outlets. We sat there under an awning in the drizzling rain on the corner of calles O y 21 drinking rum and cokes. It took a few glasses but I was catching a buzz from that crap.

George told me stories about the glory days in Havana especially when this street corner was THE place to be on a Saturday night.  Hookers dressed “to the nines,” men in dark silk suits, stretch limousines pulling in and out of the Casino Nacional all night long. When Havana was the glamorous, gambling capital of the world.

 The following night I went for a walk and found myself at the Habana Libre again hunting for pussy.  As usual, there were lots of girls sitting at the front of the building. As I walked around the circle, a girl called out to me, “Daniel.”  It was Anna from Centro Havana. Shifting back to business, I agreed to meet her Uncle Francisco the following afternoon.

The next day, I went to lunch at the Capri Hotel then headed over to the Habana Libre for my meeting. Sure enough, as soon as I approached the hotel, I saw Anna sitting in front with a large black dude. She introduced me to Uncle Francisco who looked like a smaller version of Mike Tyson. He was stocky, about five foot nine and dark skinned

Anna told me he worked as a roller at the Partagas factory in Old Havana and could get me anything I wanted. It sounded too good to be true. Only Partagas cigars or other brands as well? After every brand I mentioned, he said ‘SI.” I didn’t know that they made a variety of brands at the Partagas factory. I’d give him a shot.

We went to the Atrium for a drink and I drew up a list I needed delivered in three days. Could I trust them? If they don’t come through, my time to acquire 10 boxes somewhere else will be very limited. Anna said he could also provide me with a factura (factory receipt). Anna explained it was the blue, serial-numbered receipt from the factory or retail store I would need to show customs when I left the country.

I didn’t need a receipt last month. I just checked them underneath and that was it. Is he hustling me for ten extra bucks or is he telling me the truth.? I’m not sure, but I guess it’s better if I have a receipt just in case. I agreed to the deal and we went our separate ways. They went to work and I walked around the corner and headed for the Hotel Nacional to see if my favorite bartender Israel was working.

 That evening I sauntered over to the Monseigneur cafeteria and guess who’s sitting there?  My new friend Francisco and his niece Anna. They had a friend with them from Centro Havana named Melanis. She was a very cute Mulatta girl in her early 20s with a cute smile.  She spoke a little English so we chatted for a while and I bought her a Coke. I knew immediately she wasn’t a jinetera.

Melanis had gone to a sports school in Cuba and competed in the 1991 Pan American Games that were held in Havana. She won a bronze medal in the two-person Kayak event. She was a girl I wanted to see again.

I promised her I’d look her up when I came back to Havana at Christmas.

On my last afternoon, I was getting kind of frantic because I hadn’t heard from Francisco all day when the doorbell rang around 5 o’clock. He didn’t have the cigars with him but they were ready for pick up in his neighbor’s house in Centro Havana. He was worried about the policia stopping him if he was walking on the street with a large duffle bag. We were out the door and in a taxi within minutes.

We arrived at Calle Neptuno within minutes and went to a ground-floor house with tall doors and knocked. A man named Rene opened the door and let us in.  On the floor of the living room, all the goodies were stacked up. Partagas, Montecristo, Ramon Allones, Cohiba and even hard to find Trinidads. At $40 a box, I’m looking at a resale price of at least 8x.  I paid Francisco, borrowed his duffle bag and headed back to Manolo’s.

On my final night, I hung around the house, drinking rum and packing my red canvas duffel bag. When I finished, I went to the Nacional for one last drink. Israel was working the bar upstairs in the pool room so I hung out for an hour and made it back to Manny’s by midnight.

The following morning, I arrived at Jose Marti about two hours early. I checked the red bag with 12 boxes and went through customs with two boxes in my carry-on.  When my bag got x-rayed, the officer asked me if the bag was mine. He asked me where I bought the cigars. “Partagas Factory,” I said.

My receipt total was 1,240 dollars. He told me there was a one-thousand-dollar limit on cigars you’re allowed to depart the country with, but this time he would let it slide. Strangely, there’s a limit on the number of boxes you can export… but Cuba is Cuba.

I landed in Tijuana and passed through immigration quickly and claimed my bag. The customs agent looked at my form and told me to push the button on the traffic light. It came up green and I didn’t waste any time exiting the airport under the watchful eyes of Mexican Federale’s, local police, customs agents and who knows who else.

Joey and John were waiting for me when I came out of the terminal.  Joey told me that his truck had a hidden compartment behind the seat where I could hide my cigars as we crossed the border into the US. So I look behind the seat and there is only about nine inches of space.  Now what am I going to do?

Joey thinks for a second and smiles at me. “Just put the bag in the bed of the truck like we ain’t got nothing to hide.”

“Are you fuckin’nuts?” I replied.

Then I thought for a second and figured maybe he was right. We didn’t have much choice now and maybe a bright red bag sitting alone in the bed of a bright red truck would ease any suspicions an agent might have about hidden contraband. Guess it’s better than having him find a bag full of Cuban cigars hidden behind the driver’s seat.

At the US checkpoint, the agent ran Joey’s California license plate and asked to see his driver’s license. Then asked each of us individually where we were from. He wanted to know the nature of our trip to Mexico and we told him just a weekend of drunken nonsense in Tijuana.

The agent smiled. “You look like three hungover fools.”

We were laughing when he handed Joey his driver’s license and the gate went up. He told us to have a nice day and proceed into the “Land of the Free and Home of the Brave.”

The post Chapter Six appeared first on The Cigar Diary.

To my surprise, Manolo, or Manny as I call him, is a great chef. He made me an amazing lobster dinner. Lobster is illegal in private homes but Manny had a connection in La Bolsa Negra and only paid a dollar per tail.  He baked them with lemon, garlic, and a special sauce he whipped up. Along with a salad and rice, it was truly a tremendous culinary experience.

After dinner, I went for a walk up La Rampa to check on Rudy at the Habana Libre. Turns out it was Rudy’s day off so I hung around the Atrium and had a Cuba Libres.  The live music was a pianist accompanied by a violin. They were classically trained musicians but were unappreciated by the sparse crowd in the lobby.

During the break, I complimented the violin player and told him I was enjoying their music. He confided in me that he was trying his best considering his strings were telephone wires instead of violin strings. I promised to bring him some new strings on my next visit.

There wasn’t much going on so I finished my drink and took a walk outside. A girl sitting on the curb of the driveway asked me; of all things, if I needed cigars. Here we go again, I thought. She stood up and introduced herself in English, “Hi, I’m Anna,”

“Daniel,” I said and shook her hand.

Anna was a tall Mulatta with a large build. She claimed her uncle worked at one of the cigar factories in Old Havana and had access to all the top brands. Seems like everyone I talked to now has an uncle who works at a cigar factory.

Anna said she was originally from Guantanamo but was living in Centro Habana with her uncle Francisco. She wanted us to meet but I explained to her I had all of the cigars I needed right now, but would be willing to meet him on my next trip. Anna got a pen and slip of paper from the front desk and gave me her number.  I promised to call her as soon as I got back or from Los Angeles if I had any questions.

I went to the retail store and grabbed a couple of Montecristo #2 and took a stroll down to the Malecón. Watching the sunset with my favorite cigar. It doesn’t get better than that…  No sooner did I light my stogie when a young girl in a jean jacket approached me. “What is your name?” she asks me in broken English.

“Daniel,” I replied.

Where are you from?” she says as she sits done next to me on the wall.

“Estados Unidos.”

“How about you” I asked.

“Havana,” she replied.

“No kidding,” I said. What’s your name?”

She smiled and said, “Mislady.”

Although she was legal, she looked young so I couldn’t take her back to Manny’s house. Araceli would freak out. I asked Mislady if she wanted to go somewhere where we could be alone.

“Si, casa de la abuela” she said.

Her Grandmother’s house? This place is fuckin’crazy. Well, so much for a relaxing night a home, I said to myself. It’s really hard to focus on business here when there’s so much pussy walking around, it’s just hard to say no. I guess I was suffering from what locals called “Cuban Fever.” I flagged down a taxi and we drove in the direction of Old Havana.

We got out on a side street off the Prado and walked to a high-rise apartment building. Up two flights of stairs, Mislady knocks on a door. A grey-haired, bespectacled white woman in a drab gray housedress opened the door. Mislady brushed by her pulling me by the hand.  I embarrassingly shook the Granny’s hand and introduced myself.

She knew why we were standing in her living room and I’m sure I wasn’t the first fish that little Mislady reeled in brought to Granny’s doorstep. Granny playfully slapped me on the shoulder and called me, I’m assuming a “naughty boy” or something similar that made Mislady laugh out loud. Granny walked out the door and shut it behind herself. Mislady took off her jacket and sat down on the couch.

She was a young, petite mulatta girl and although she was blessed with light skin, she had thick kinky hair that Cubans refer to as “pelo malo.” She wore it pulled back into a short ponytail. Probably a couple of generations removed from her African heritage but I think ol’ granny may have “pulled a boner” back in the day. No pun intended!

Without any small talk, Mislady and I began to softly kiss. I slid my hand under her t-shirt and cupped her little, braless titties, running the tips of my fingers over her nipples until they became hard and erect. I didn’t want to fuck her with granny snooping around so I motioned for her to take off her pants.

She didn’t hesitate to peel everything off including her panties. She spread her legs as wide as possible, exposing her little pink gateway to heaven. Without missing a beat, I slid off the couch onto my knees and pushed my wet tongue into her tight little pussy and began softly licking her little slit from north to south and east to west.

As her big brown eyes began to close, she leaned her head back on the couch and began to hump her groin up and down on my face.  We found our rhythm and as she’d thrust her hips down, I licked up over her clit and caught it again on the way back up. She was far away now, in a blissful state, somewhere close to heaven.

She pulled my head closer and rubbed her cunt on my face faster and faster, then gave a little moan when she came and whispered, “Dios.” I didn’t want to stop and continued to lick her little sensitive little clit side to side as fast as I could until she sat up shaking and pushed my head away from her throbbing pussy. By this time, my cock was so hard I could barely stand up.  It was my turn.  As she looked up at me with those wanton, loving eyes, I pulled my pants down and let my erection stand and breathe.

My little lady leaned forward and took my cock in her hand and guided it into her mouth. The feeling of her warm mouth around my hard shaft was amazing. She sucked the head in and out of her mouth as she stroked the shaft in perfect rhythm. Moments later, I put my hand on the top of her head and fucked her mouth, blasting a hot load into her gloriously warm, wet mouth. She didn’t hesitate to swallow. I flopped down on the sofa next to her feeling spent.

I could have sat there all night but I wanted to be gone when little old Granny returned, so I handed Mislady the twenty-dollar bill from my shirt pocket. I told her that I had to vamos and we could meet Manaña at the same time, same place. I gave her a peck on the cheek and walked briskly down a flight of stairs to the dirty, dark street below.  As a car passed, I yelled “Hotel Nacional” and he stopped on a dime. A man said “Vamos” out the passenger window and away we went.

The following morning knocking on my bedroom door woke me out of a sound sleep.

“Daniel,” said Malagra. “Tu amigos aqui.”

“Ok,” I mumbled.

I peeked through the door slates and saw George and another guy sitting on the sofa in the living room. I pulled on some shorts, splashed water on my face and went out to greet the Jineteros.  George and his sidekick jumped off the couch and came into my room with a large canvas bag.  I didn’t catch the cigar guy’s name but he had an x carved into his forehead that I wouldn’t soon forget.

They started pulling boxes of cigars out of the bag and stacking them on my bed. It was like a fucking mirage. Romeo Churchill Tubos, Ramon Allones, Montecristo #2, Montecristo #1, Cohiba Robustos, Cohiba Esplindidos, Partagas Serie D. #4 etc. Fuck, I’ve hit the jackpot.  Boxes virtually impossible to get in the States. George claimed they were all factory cigars and not to worry about the quality…which usually means you have to worry.

He was only asking $50 a box. I didn’t give a damn if the cigars were rolled in Alaska as long as they were good. George had earlier quoted me prices between 25-40 dollars. They tried to put the “Bogart Squeeze” on me but I didn’t care. George spewed out some crap about the great quality and the fact that all the boxes have factory stamps on the bottom to prove they came directly from the factory.  I’ll have to look into all of this later but for now, I was happy.

Georgie had added a higher commission which bumped up my prices.  Still, $50 a box is a great price if these are factory cigars. Just on principle, I beat them back to $45 per box anyway. The total order came in under $300 and I knew the resale price would be almost 10x, so what the fuck!  As soon as I paid them, they were out the door.

Anyway, I had my cigars and only two nights left in Havana so I went out on the town. After a couple of pops at the Nacional, I made my way over to Monseigneur Cafeteria. My buddy Alfredo was in the middle of his 12-hour night shift. He was a nice kid who spoke English so I sat at the counter and we shot the shit.

When I got back to Manny’s house, he was sitting on the front steps of his building with a young lady. He was obviously waiting for me and introduced me to Tonya and told her I was Daniel from California. I was taken aback and figured that Manny had known her for a while.

She was white, 20ish with beautiful auburn hair which gave her a wholesome, natural look. I knew immediately she was different than the other girls I’d been with She was alive, vibrant with a spirit that was uplifting and contagious.  This wasn’t just a job to her.

I threw her on the bed and gave her a playful slap on the ass which she immediately returned. We sat at the foot of the bed and looked into each other eyes. When we kissed it brought me into the moment. There was nothing else, only the heat of her kiss. It gave me a tingling sensation that’s hard to describe but different from the other girls. A moment that would last forever

We laid on the bed and I began to undress her. She reached into her purse and pulled out a condom. I took it from her and threw it on the floor. She giggled as she stood and removed her underwear.  We never fucked. We began what seemed like endless hours of lovemaking.

When the room began to grow light, her head and was on my chest, her wavy auburn hair covering me like a warm blanket of love. She told me she had a son at home and needed to leave. As she took a shower, I walked over to the Nacional and changed a hundred. When I got back, she was dressed and sitting in the living room.  I handed her two folded twenties and walked her outside.

I kissed her on the sidewalk and asked her again to stay. She said her mother would be worried and promised to return later that evening. The sky was turning blue as we hugged and said goodbye.  I stood there and watched her walk up the street past the Hotel Capri and the ice cream park. I walked across the street to the Nacional with sixty dollars in my pocket and Tonya on my mind.

I was all packed up and ready to go when George and his driver Angel arrived the next morning to take me to the airport. Manny gave me a shot of rum to soothe my nerves and I lit a cigar for the ride. It’s funny, but on the way to the airport, you hang on to everything you see like a kaleidoscope of images burnt into your soul.  Girls walking in the street, children running, men playing dominoes, the sounds of trucks and horns and salsa. The multicolored shacks, bars on windows, even the litter in the street you somehow take with you back to wherever you’re from.

I hadn’t even left yet and I already missed this place. We rambled along in Angel’s faded brown 80’s Lada and made it to the airport by 9:30 for my 11 o’clock flight to Cancun.  As we pulled into Jose Marti, the usual crowd of onlookers were standing at the exit door, waiting for salvation to arrive. Nameless faces of all ages, sizes and colors mingled together. I get out of the car and pull my suitcase and large red duffle bag out of the trunk.

“Twenty -six dollars,” said. George. “And he’ll be waiting for you the next time you arrive.”  I hugged them both, wished them well, and filed through the crowd into Terminal No. 2.  I grabbed a can of Chrystal on my way in and took my place in line.  As the line moved forward, I felt a mild anxiety building in my stomach. What if my cigars get lost? What if Mexican customs take them? Think positive thoughts I tell myself.

I checked my suitcase with the cigars underneath, got my boarding pass, and slipped through Immigration and customs without a glitch.  I buy another beer on the other side and sit down near my gate. Sitting next to me is the former Black Panther and devoted Commie Angela Davis.  She is on my flight to Cancun.

Before I knew it, were boarding. The flight is only long enough to order one Cuba Libre before we start our descent into Cancun International Airport.  Cancun is a sea of humanity with international flights landing every hour.  I grab my stash and stand in another very long line leading to immigration. My anxiety level is rising now. Mexican Customs has this silly traffic light with a green and red light on it.

After the agent examines your customs form, each traveler is required to push a red button on the traffic light. If the light blinks red, you’re being searched. If it blinks green, you’re free to go. It’s a crap shoot here. I know if I press Red it’s over. It’s the end of the cigar business and the party’s over as far as ever going back to Cuba.  The agent takes my custom declarations that specifically ask you to declare all tobacco products.  I push the silver button on the traffic light blinks… GREEN.

I take a sigh of relief and check in at Mexicana Airlines for my boarding pass for Los Angeles. Back upstairs my boys are waiting for me. Jose, Jose and Augustine are bartending at the Lion Bar. I immediately ordered a corona and a shot of Cuervo Gold Tequila. Before long I’m boarding Mexicana Airlines flight #947 for Los Angeles.

The fight to Los Angeles takes almost five hours. I arrived at LAX around 9 pm and we were forced to wait on the tarmac for about twenty minutes until a shuttle arrived to take us to the terminal.  Once the shuttles are full, we’re whisked off to Tom Bradley International.

I’m feeling a little nervous as I walk through the maze of stairways that leads to immigration. I’m looking to the left and right for an open door to sneak out but there are none. It’s the final checkpoint of the trip and probably the most difficult one to get through. Customs agents in the US are like military police. Most are ex-military. I have to be strong. Maybe I had too many drinks on the plane. It’s hard to swallow.

My bag drops down the shoot and I pull it off the turnstile and throw it on my cart. I partially unzip the bag with cigars and pull a handful of clothes partially out of the zipper to show I’m not trying to hide anything. I take a deep breath and walk to the first customs checkpoint.

I handed him my declaration form and birth certificate. Since we don’t need a Passport to travel to Mexico, I tell the agent I’ve been fishing in Mexico for the past week. On the back of the form, I scribbled a list of purchases I made in Cancun. Shoes, magazines, books and crap like that.

“Nothing to declare?” he asks. The officer looks through my eyes and into my soul. “No,” I reply. What was the nature of your trip?”

“Fishing.” He hands my paperwork back and tells me to proceed to the next checkpoint.

At the last stop, the agent takes the form. It’s the last stop.  I try to look as nonchalant as possible. He took my customs declaration and asked me if I caught anything. I’m startled for a second and I continue walking then realize he was referring to my trip to Cancun.  I yell back “Yeah, a cold!”

I made it! What a feeling!!! I walk up the ramp and into the crowded LAX International Airport terminal feeling like a million dollars.  My brother is waiting there to greet me. As he’s walking toward me, I give him the thumbs up. We drive along Pacific Coast Highway and wind up into the green hills of Rancho Palos Verdes. “I have so much to tell you,” I say. “You won’t believe it.” “Can’t wait to hear it,” he says. “But first thing tomorrow, book your ticket for Havana.”

The post Chapter Five appeared first on The Cigar Diary.

I woke up excited the following morning knowing full well my entire day would be filled with more life-changing adventures. After a light breakfast at the hotel, I jumped in a taxi and went directly to my 12-noon meeting with my new friend George. Since he made that crack about “American time,” I didn’t want to be late.

As I approached the Plaza, I could see George in his usual spot dressed in a white shirt and dark pants chatting with a man who looked like a tourist. George’s ability to speak English gave him a marked advantage over the competition.  When he spotted me walking up the Prado he started grinning from ear to ear.

“How you doing today, Danny?” he said as I approached. “You’re a man of your word. 12 o’clock sharp” I didn’t fully understand the significance of arriving on time for our appointment. For whatever reason, punctuality is not in the Cuban’s vocabulary. They arrive for an appointment when they arrive. Their motto is “I’ll be there when I get there. If I don’t get there, I won’t be there.”

George flagged a taxi and we made our way down the Prado and drove west on the Malecón. The Malecón is a captivating experience in itself. It stretches roughly five miles along the city’s North coastline bordering the straits of Florida. It seems to be the social hub of the city and maybe a symbol of Havana itself. The crashing waves, the salty sea breeze, and out there, somewhere beyond that endless horizon represents freedom for most Cubans.

It’s the architecture along the street that attracts me as well. A mess of Colonial and Art Deco styles that once made the Malecón the envy of the Western world. Now weathered, decaying, lost in time, a metaphor for the decay of a once noble attempt to bring equality and justice to an impoverished nation.

The young people gather there. Full of hope, sitting on the wall, young lovers embraced against the tyranny of daily life. Just a bottle of rum, music, and their bleak lives are temporarily forgotten, peacefully engulfed by the sun and the sea.

We turned left up 23^rd “La Rampa” and went around the block, made a right down 21^st street, and stopped at a building across the street from the Nacional.  We walked up a flight of marble stairs and into an art deco building. There was a beautiful marble sculpture of a naked David in the lobby.

We went up to a flight of stairs and rang the doorbell of the first apartment at the top. A few moments later the door opened and a lovely 40ish woman greeted us and invited us in. From what I gathered, George explained to her that I was staying at the Habana Libre and found it was too expensive.

This was a nice-sized apartment with three bedrooms. There was a small balcony with a perfect view of the Hotel Nacional directly across the street.  We sat down in the living room and she returned a few minutes later with coffee.  She told George that her husband would be home shortly so we took our coffees out on the balcony.  George’s son had gone to school with the owner of the house. He had just begun to rent rooms to tourists.

About 10 minutes later, a man walked into the living room with black hair and a bushy mustache and introduced himself as Manolo or Manny. I introduced myself as Daniel and in Spanish, it’s pronounced like ‘Danielle’ in the States. He spoke a little English, enough to be understood.

The first room he showed me was larger with a private bathroom. I thought it was funny he pointed out the room had hot and cold water. Don’t all apartments have cold water? I didn’t realize hot water was a big deal. Manolo explained that almost all Casas are equipped with an electric shower head, made in Brazil, which warms the water by about 10 degrees.

It turned out I liked the smaller room in the front of the house facing the street. The toilet was in the shower or vice versa, but I was as happy as a pig in shit. I knew I’d found a home here. Manolo, his wife Araceli, and his two sons Ariel 8, and Manolo 10 live here but he assured me I wouldn’t be bothered.

Manny told me not to worry about having my own key. “Just ring the doorbell when you come home at night, and I’ll get up and let you in,” said Manny.  He didn’t know who he was dealing with. Once the rum started flowing and I started my shenanigans, back and forth, in and out, one girl after another, it began to drive him nuts. “Daniel is crazy,” I heard him say to a visitor. By day three, I had my key.

There’s a bar directly across the street called the Monseigneur. It’s below street level, a French-themed restaurant and bar and there is also a cafeteria attached next door with a counter. Opened in 1957, the interior had that old Las Vegas feel to it.  The barman spoke pretty good English. His name is Efrain and he’s been the bartender there since the early 1960s.

The greeter stationed in the front of the Monseigneur is Michael. Very friendly and extremely humorous. He has an uncanny resemblance to singer Johnny Mathis. He speaks English and seemed to be a nice guy and someone I’m sure I’ll get to know a lot better as time goes on.

Big George is turning out to be a very interesting person himself.  He had worked for mob boss Meyer Lansky  in the late 50s. He was the official limousine driver for the hotel when Havana was the glamour and gambling capital of the Caribbean.

Before he worked for Lansky, George was a taxi driver in town and had known everyone in the golden age of the city. He eventually got a job at Lansky’s Hotel Riviera when it opened Christmas 1957. George claims that he never knew about Meyer Lansky’s background and only knew him as the floor manager of the Riviera.

According to George, Meyer was as cool as a cucumber. He was soft-spoken and never raised his voice. Always immaculately groomed, Lansky got a haircut and a shave every morning in the barbershop. When George drove his boss around town, Lansky liked the radio on the lowest volume.

Lansky once caught George playing the slots and said to him, “How many kids you have George?“Seven, Mr. Lansky,” replied George.“Well, if I catch you gambling again George, I’m going to fire you,” said Lansky.

“Gambling is a losing game, George. Now go home and take care of your family.’

During his tenure at the hotel, George picked up lots of mob figures but never knew any names. Some of the Hollywood celebrities he recognized like Ava Gardner and Gary Cooper. He was sent to the airport late one night to pick up Frank Sinatra.

“Sinatra had two requests,” said George. The first was where can could get some “snow” and if he knew anyone who could sew patches on the sleeves of his sports coat, which was in fashion at the time.

He crossed paths with his idol Nat King Cole when Nat played some gigs at the Hotel Riviera and Tropicana. He frequently saw Hollywood actor George Raft who was the official greeter of the Hotel Capri Casino on the same street as Casa Manolo.

When Fulgencio Batista fled the country on New Year’s Eve 1959, the Casinos were ransacked and forced to temporarily close. When the Casino Dealer’s Union protested, Fidel reopened them for about a year. The Cuban government finally nationalized the properties in March of 1960 and then closed them for good in October of the same year.

George related an anecdote that was so unusual it made me stop in my tracks. George claimed that he may have been the only person to ever see Meyer Lansky cry. I stood silent. The only word I could mutter was “cry?”

“That’s right Danny,” said George. “Shortly after the casinos were closed, Mr. Lansky called me one morning and asked me to drive him to the airport. When I arrived at his apartment on the Malecón, he was standing on his balcony, looking out on the sea,” continued George. When Mr. Lanky turned around, he had tears in his eyes. He said, “George, I won’t be coming back this time. Castro doesn’t want me here.”

“I tried to convince Mr. Lansky that the casinos were only closing temporarily and soon everything would go back to the way it was,” George continued. “Lansky just turned around and stared out at the water across the street.”

“That morning I drove him to the airport and never saw my boss again,” said George. “Of course, he was right. That was the end of gambling in Cuba. It wasn’t until a year or two later that he found out who Mr. Lansky was. All I knew at the time was that the owners of the Riviera were Messrs. Ben and Harry Smith, two brothers from Canada.”

George has been hustling around Havana ever since. The only official job he mentioned since the revolution was the few years he worked on the resort island of Cayo Coco. I’m sure his English skills were a big part of his job there.

All these years later he’s still on the hustle. Cuban workers only earn between 15 and 60 dollars a month, so to survive you need to be in La Bolsa Negra. Translated this means “the black bag.” If you want to be able to buy anything besides the bare necessities, all Cubans have to earn money in the black market. I’ve been told that La Bolsa Negra represents about 80-90% of the Cuban economy.

Manny introduced me to the word Jinetero/Jinetera for the first time. It means rider. Riding off of someone else like a tourist. I guess George is considered a Jinetero. He’s on the street every day hustling tourists, so he fits the profile.I’m sure he made a few dollars in commission on the introduction to Casa Manolo, but for $25 a night, who cares?

Since Jinetero George has a connection to just about everything in Havana, I casually asked if he had a good cigar connection. Of course, even if he didn’t, he’d say he did.

“There’s a young man in my vicinity,” said George. “He works at the Partagas factory as a roller and can get you as many cigars as you want out the back door at a very good price.”

“What kind of prices are we talking about George?”

George smiled; he knew he had me on the hook.

“Let’s say between 25 – 40 dollars?”

“A box?” I inquired. “Any brands and sizes.”

“That’s right Chico,” said George.

If this was true, I just struck gold. I could sell the cigars back in Los Angeles for ten times that price. If I could just figure out a way to get them back safely. It’s tricky at the airport. Over a certain number of cigars, customs require official receipts from a state store. If I bought these on the street, there wouldn’t be receipts.  How could I get receipts?

Still, I was drooling at the thought of it.  My favorite brands directly from the factory. Montecristo #1, Romeo y Julieta Churchill Tubos, Hoyo de Monterrey Epicure Seleccion and even the hard-to-find Montecristo A’s. I told George to talk to his guy and set up a meeting ASAP.

As soon as night fell, I took a shower and walked over to the cafeteria to grab some beers. Walking back with six cans of Chrystal rolling around in a cardboard box, I was approached by a beautiful young girl with dyed blonde hair who asked me where I was going. “Mi casa,” I replied, pointing to the building across the street.

“Y tu?,” I asked.  She just smiled.

She was very young and very petite, maybe 5’ 1 and about 100 pounds. I felt a little uncomfortable standing on the street corner with her. I pointed at her and then to myself and said “You go with me? Mi Casa?” and pointed across the street.  She nodded her head and stuck her arm out at a passing taxi that stopped on a dime.

Before I had a chance to explain where my house was, I was in the back seat of a taxi going to who knows where with this gorgeous little girl. We drove about five blocks and got out. I paid the driver three dollars and we walked up a flight of steps and into an apartment building.

The girl is walking ahead of me and stops at the first door and knocks. An old man answers and he knows this little twat.  We walk in and sit down on the sofa; I’m still carrying the box of beers in a cardboard carton. I offer the old man one and of course, he takes it.

He speaks a little English and tells me the room will be 10 dollars. OK, now I know why I am sitting here. The girl looked young and I was feeling a little embarrassed but this old prick could give a fuck as long as he got his sawbuck. If I walked through the door with His daughter, he wouldn’t have cared less.

We all stand and I hand him the money and he walks us down a hall to a bedroom and opens the door. Once inside, I crack a beer and give one to the girl.  Less than a minute later she walks out of the bathroom naked and climbs into bed.

I shut the light off, shed my clothes, and climbed in next to her and we started to kiss. There is light coming in from the street filtered by the soft curtains on the window. I turn on my side and we hold each other. She smelled like lavender and her skin was as smooth as silk.

I pull down the blanket and start sucking on her pert little nipples and she arches her back and begins to moan. She’s so young and pretty, I had to lick her little pussy for everything it’s worth. I work my big finger in and out of her wet little twat and begin rubbing her clit.  This was unbelievable. As I mounted her and she opened her legs wide and we fucked each other into bliss.

After an hour or so, she gets out of bed and turns on the light. I lay there looking at her young, tight body and beautiful little ass walking to the bathroom. It’s an image I’ll never forget. She got dressed and slipped on her heels like she was in a hurry or something. Suddenly the spell was broken and I began to think “fuck, this could have been some kind of a setup.”

I got up and found my clothes strewn around the bed.  Suddenly, I was anxious to get the fuck out of there. She’s young and I had a vision of her father bursting into the room and demanding five thousand dollars or he’s calling the police.

I grabbed one of the green cans of Cristal sweating on the dresser and opened it. I got dressed fast and gave the girl a 20 spot as we walked through the house and out the door at a brisk gate. I felt as if I had just committed a crime or something-maybe I did. On the street in front of the building, I gave her a quick kiss and said “Manaña, ocho, Monsignor.” She smiled and said “Si.”

I looked around and noticed the bell tower of the Hotel Nacional which appeared less than a mile away. She walked in one direction and I began walking in the direction of the Nacional wondering if I had enough money left for another six-pack. The house was closer than I thought it was and I was back in the safe haven of Casa Manolo’s before I knew it.

Manny’s house turned out to be a great find. Even the building is amazing. A six-story art deco design that was built in the late 1940s by a doctor. Manolo has a kind black woman named Malagra who comes in during the day and cleans the house. It’s a perfect situation for me. I’m invisible to the family and can come and go as I please.

I felt an immediate connection with the family, it kind of gave me some protection from the elements of the city. I was still naïve about Havana street life and would later hear some “Whore” stories about guys getting all of their money stolen by one of these Jineteras.

Some interesting characters are living in the building as well. A woman named Lilly lives across the hall. She grew up in the States and moved back to Havana during high school. There is a crazy son-of-a bitch named Richard who lives on the 4^th floor of the building. He has a bright smile, sparkling eyes, and several gold teeth.  He insists on calling me “Jack Daniels.”  Of course, he can get me anything I need.  I’m sure we’ll do some business down the road.

On the first floor near the entrance is Armando who is somewhat of an intellectual. His house is also a Casa Particular, His parents sit in the front window all day looking for renters. Armando knows Manny from school and is trying to become a professional writer. There t also a guy living upstairs named Silvio who looks exactly like the former heavyweight coxing champion Floyd Patterson.

 As far as location, I’m across from the Nacional for a good meal and a short walk to the Habana Libre. Lots of other places to eat nearby including a couple of new paladares that opened up the street. The government is allowing Cubans to turn their houses into restaurants to help serve the increasing demand from tourism.  They’re required to pay a monthly tax to the Beard.

Besides the hotels and paladares, there’s a restaurant down the street for cheap lunches called Wakamba. Once a famous Chinese restaurant in the 1950s, it’s a cafeteria now that serves Cubano sandwiches and spaghetti for a couple of bucks. Across the street from Wakamba, in front of Hotel St John’s is a small outdoor espresso bar for great coffee and cookies.

This is my world now and these are the people in it. If I can get the product home safely, I’ll be back again next month.  There are a few things I need to figure out first. Where to get the best product at the lowest prices and how to get it out of here. Since everything could be found in the La Bolsa Negra, I wondered if could get some official factory receipts there too to allow me to clear customs. It would take some legwork, but somehow, someway, I will figure it out.

The post Chapter Four appeared first on The Cigar Diary.

It had been about two years since my sexcapades began in Havana and now there was a cigar boom taking over the country. Magazines like Cigar Aficionado and Smoke Magazine were on the newsstands and everyone was jonesing for a Cuban stogie. The demand was crazy and buyers were willing to pay just about anything for an original Cuban.

My brother was working in the financial world and had a lot of high-end clients who wanted to buy Cubans cigars; for bragging rights if nothing else.

So, one day he says to me, “Listen, if I give you $3,000 could you go back to Havana and bring back 12 boxes of cigars?”

“Hell yeah,” I said excitedly.

“OK, order your tickets,” he says, “and let me know when you’re ready to go.”

I repeated the same routine as my first trip. I ordered my visa from the Embassy of Switzerland in Washington DC and made a run down to Tijuana to pick up my airline tickets from the Montfort Agency.  I decided to fly to Cancun this time. From there, it’s only a 50-minute flight to Havana. Before I knew it, I was on my way to the airport.

Arriving in Cancun, I was stunned by the heat as soon as the door of the plane opened. Had to deal with another 24-hour layover so I made the best of it. Weaving through the busy traffic and the heavy heat of the Yucatan, I made it into town and rented a small hotel room in the downtown area.

Carrying three grand in cash made me a little uncomfortable. I checked into a small motel, hid my money in the ceiling light, and went out for an authentic Mexican dinner and a couple of beers.  At a little Cantina near the the motel, I played a couple of games of pool with the locals and sat at the bar and drank tequila shots and Corona’s. It was late afternoon and the sky was turning dark blue when I stumbled back to my room to check on the money and have a short nap.

Later  that evening I went back to the Cantina for a drink. A kid asked me if I wanted to play a game of pool, so I shot a game with this local Mexicano. He bought me a beer when I won and I bought him back then he won and it became a back-and-forth thing for a while but I was getting a little suspicious. This kid was overly friendly so I told him I had to make a phone call and I’d be back later.

I got up the next morning and had a free continental breakfast at the motel.  Check-out was 1:00 pm so I asked the hotel manager if I could keep my bag behind the counter until 4 o’clock because my flight wasn’t till 7:30 pm. He agreed so I jumped in a taxi and I went down to a small bar on the ocean and I had an inexpensive, albeit amazing lobster dinner.

The lobster, grilled in butter cost eight dollars. Of course, I had a couple more beers and looked at surfing memorabilia and photos of locals on the walls of the restaurant.  I got back to the motel around four and grabbed my bag from the motel. I flagged down a taxi for the airport and asked the driver for a special favor.

I said, “Excuse me, I still have three or four hours before my flight leaves would you mind hanging out with me for a few hours and I’ll buy you dinner and drinks and give you a flat rate of fifty bucks?”. He agreed, so we bar-hopped for a couple of hours, had a few appetizers along the way, and I got dropped at Cancun International Airport in time for my 7:40 flight.

My AeroMexico flight took off on time and I arrived at Havana’s Jose Marti Airport about an hour later. I got through customs and immigration quite easily and my bright red duffle bag dropped down the shoot and onto the turnstile after about 25 minutes.

The Customs officer took my form, glanced at it, and waved me through without a glitch. As I walked out the door of the airport a HavanaTour taxi driver approached me, “Need a ride?” he said in English.

With a surprised look on my face I said, “Yes, going to the Habana Libre Hotel.

He opened the door of his taxi and grabbed my red grip and shoulder bag and threw them in his trunk. He opened my door and I jumped in and we drove off into the warm, dark, Havana night.

He said his name was William and I asked him, “Do you know where the Habana Libre Hotel is?

He snickered to himself he said, “Of course, I’m from Havana”

After about a 25-minutes we pulled into the driveway of the hotel in the Vedado district of Havana. The Habana Libre was only a block away from Hotel Nacional and a lot cheaper.

The Habana Libre was built by the US puppet President Fulgencio Batista in the late 1950s. Conrad Hilton was even at the grand opening in ’58. At the time, it was the tallest hotel in Latin America. There’s a pool on the second floor and home to the world-famous Trader’s Vic’s. Fidel nationalized the hotel in the early days of the revolution.

Pulling up to the front door I noticed that the driveway of the hotel was loaded with a mob of young girls. It’s a large circular driveway and inside the circle, about 100 girls were sitting around smoking cigarettes and chitchatting and I was left wondering what the fuck was going on here tonight.

I asked William what was happening and he just looked at me nonchalantly and said, “What do you think; it’s Saturday night in Havana.” Oh my God, I said under my breath. I have never seen so many beautiful girls sitting around at one location for no reason other than it’s Saturday night.

I went inside and checked into the hotel. I rented a wall safe behind the front desk and stored my cash.  After a shower and a change, I made a beeline back outside to take a look and see what’s what.

I walked around the circle and saw a beautiful girl with dark features in her early 20s. I asked her if she would like to have a cerveza.  As I took her by the hand and started walking her back into the hotel, a skinny black girl popped up out of nowhere and pointed to my girl and said “Amiga, Amiga, and invited herself to join us for una cerveza?

I just smiled. “Ah, what the fuck,” I said, “come on.”

We sat down in the large ground-floor atrium that had white metal chairs and tables and ordered some drinks. There were couples scattered around the floor having cocktails and an unappreciated pianist playing Chopin under the staircase. Suddenly, out of nowhere, a waiter walks up to me and says in English, “What can I get for you, sir?”

What luck! Another person on the same night who spoke English. He introduced himself as Rudy and took our order. I ordered a Cuba Libre and both girls ordered Hautuey Beers. Well after a couple of rounds, I started to wonder how I was going to get these two lusty little bitches back upstairs to my room on the 12th floor.

I introduced myself as Daniel and the black girl shook my hand and smiled, “Elisa” and the white girl said “Liset, mucho gusto.” I motioned to Rudy for another round and told the girls I’d be back in uno momento.

They sat there, watching me like a hawk as I walked around the perimeter of the lobby looking for a way to solve my dilemma.  Then I noticed on the back wall near the elevators a fire escape stairwell door hidden by a large palm tree in a pot. I opened it and saw the staircase leading up to the 12th floor. Bingo!

I went back to the table to share my discovery with the young ladies.  I pointed to the stairway door and then toward the ceiling.  They nodded their heads and smiled.   “Doce,” I said and spelled the number 12 on my palm with my finger. They smiled again and repeated it “Doce.”  “Si, I said. Cuarto doce, doce,” and spelled out the number 1212 on the table.

I finished my drink, pointed to the ceiling again, got up, and went to the elevator. On the 12^th floor, I opened the door to the stairwell and waited nervously. Several minutes later I heard the sounds of girls giggling in the stairwell and I knew the plan was working.

As they came out of the fire escape, I was standing in the doorway of my room looking up and down the hall to make sure the coast was clear. My room was a few doors down from the stairwell and as I waved, they came running down the hallway laughing and leaped inside. I closed the door behind them and listened for any sounds in the hallway.

We fell onto the bed, kissed each other for a while, and played around until I got up to order some drinks.  I called downstairs and asked for 2 Cuba Libre’s and 4 beers.  As we waited for the drinks to arrive, the girls went into the bathroom and showered together.

With the sound of running water in the background, I stood in the window and looked out over the glittering lights of Havana. Down on the second floor was a large pool and then beyond that was the glittering lights of

Here I am again I thought, back in the forbidden land of Cuba Libre’s and Montecristo’s.  My first night and I’m in an air-conditioned room with two hot girls and we’re about to fuck each other to death. Am I dreaming?

My spell was broken when the girls emerged from the bathroom with just towels wrapped around them. Liset graceful and dark-haired, grabbed a towel and began to pat her young breasts. They sat down on the bed and Liset opened her purse and pulled out a red pack of Hollywood cigarettes. There was a knock at the door and they jumped back into the bathroom.

I signed for the drinks and called them out for a cold one. They just sat there on the bed, smiling from ear to ear, their backs against the headboard. I took off my shirt and climbed in between him wearing only my thin cotton shorts.

We sat there sipping our drinks until Elisa put her beer on the nightstand, turned back, and started kissing me as Liset started to untie my shorts. It was the first time I had been with a black girl and I liked it. It was a little kinky which added to the experience.

Liset was a beautiful Latina with long, jet-black hair, alabaster skin, and dark eyes. Of course, by now my dick is as hard as a rock so she took it in her hand and start stroking it.  Then she devoured and I felt myself growing big and hard inside her mouth. Nice and wet, she slowly sucked the head in and out of her mouth while I’m still deep kissing Elisa.

When the towels came off I laid on my back. Elisa climbed up on me as Liset rubbed my chest and kissed me passionately.  Elisa pushed my cock into your pussy and just began slowly riding it  up and down, up and down in a slow rhythmic motion. I couldn’t wait to feel myself inside Liset. I didn’t have to wait long.

After about five blissful minutes Elisa rolled off and started passionately kissing me. Liset didn’t miss a beat. She took over where Elisa left off and rode me in a smooth up-and-down rhythm.  It was as if they were a well-rehearsed tag team. Maybe they were… Up and down, up and down, up and down motion that gave me a feeling of ecstasy that I had never experienced before.

Time to change positions. They alternated lying on their backs and I’d take them in the good ol’ missionary position that allowed me to push myself deep into their love shaft. When I’d lean back on my knees one nympho would slide out and the other one would slide under and take her place.

When I leaned back against the headboard to take a short rest they took turns sucking my cock and licking my balls. We fucked from every conceivable position and angle I could think of and a few I’d never thought of before. The first time I looked at the clock it was 2:26 am.

We took a break and I went downstairs to the 24-hour cafeteria and got us some sandwiches. When I returned, they were sitting up like two hungry puppies waiting for their master to return. We devoured the snacks on the white sheets and before long we were playing again, crumbs and all, kissing and fondling until we finally fell asleep sometime near dawn.

I woke up between the two ladies like three spoons in a drawer. It was 8:00.  The girls started to move around and Liset climbed out of bed and went into the bathroom. As soon as I heard the shower running, little Elisa started tree climbing again, back up on my hard cock and we started all over again.

Like clockwork, when Liset came out of the bathroom, Elisa climbed off my dick and went in the bathroom. I thought it was rest time, but who was I kidding? Liset took off her towel and with her wet hair dripping on my chest she took over where Liset left off and pushed my cock into her pussy and started riding it.

It was close to 10 before the girls were showered, dressed, and ready to hit those dirty, rotten streets of Havana. I went to the closet and pulled out 2 twenties and 2 fives and handed it to them. They smiled and couldn’t have been more thrilled if I’d handed them a thousand dollars wrapped in a red ribbon. I told them to come back esta noche at ocho. They gave me a thumbs up.

I opened the door and looked up and down the red-carpeted hallway. At the far end of the hall  a maid’s cart was parked so I motioned that the coast was clear. They kissed me as they left and ran into the stairwell giggling. I went back to and fell back into bed.

After dozing back to sleep for about 2 hours, I dragged my sorry ass into the shower and then went downstairs to the cafeteria and had some bacon and eggs. It was time to go to Old Havana and begin my mission of finding the list of requested cigars at the best prices.

As soon as I walked outside, a cabbie waved to me and I said “Partagas Factory“ and jumped in the back seat. As we drove down the Malecon, the Gulf was a deep blue and a stiff breeze caused white caps to roll over the waves. Young people sat on the wall, dreaming of better days.

We turned right on Paseo del Prado, once considered the most beautiful street in the world. I told the taxi to stop at the curb and got out to walk along the tree-lined promenade with its bronze-sculptured lions, coral stone walls, and marble benches that offered a glimpse into the beauty and majesty of Havana’s past.

In the distance, I could see the El Capitolo building with its dome top modeled after the Capitol building in Washington. When I reached Hotel Plaza, I went inside to the lobby bar and ordered a beer.  After a couple of pops, I continued up the street several blocks, and directly behind El Capitolo, lo and behold, I found the Partagas Factory.

The factory is a four-story building with Partagas 1845 written on the top. I walked through the front door and into the world of the cigar roller torcedor and not being mistaken for a roller, I was directed into the retail store with their large display cases. Various brands and sizes of cigars were stacked to the ceiling. I was in Heaven.

They had everything I was looking for including H. Upmann, Romeo y Julieta’s, Punch, Bolivar, and Ramon Allones. They also carried a wide variety of Montecristo, Ramon Allones, and a variety of different brands with boxes ranging from $125 up, depending on the brand and size. I knew I was in luck. I could fill the order and stay within my budget.

After an Espresso at the bar, I lit a Romeo Churchill and started my trek back to the Prado. I figured I’d have another cocktail or two at the Plaza. Through the cut-glass doors, I walked into another time, into the 1800s with its white marble floors, lobby statues, and stained-glass bar. I ordered a Hatuey beer and enjoyed my cigar.

After a couple of beers, it was time to head back to the Habana Libre to plan my night. Out in the September heat again the sidewalk of the Prado was a river of faceless faces. Some glanced at me with curious eyes. Most were lost in conversation about the heat, food, or the difficulty of life. If they knew I was an American, their gazes may have lasted a bit longer and deeper.

My mission was interrupted by a voice “Welcome to my country.” I paused and turned around to find a tall man framed by the haze of the sun.  Stepping into a shadow the silhouette became a large black man with a wide bright smile and pure white hair.

Speaking English, I assumed he was a foreigner like myself. I stood there, looking a bit surprised “Where are you from?”

“Right here, Cuba”, he replied. “this is my country”.

“Just curious,” I said, “but where did you learn to speak English?

He reached out his big hand and introduced himself, “George McCatty, ‘service with a smile,” and started his pitch.

“My parents are Jamaican,” said George.  “English was my first language, even before I learned Spanish. I grew up in Camaguey but I’ve been in Havana since the 50s. Where are you staying, asked George?”

Although my street sense made me a bit cautious, George’s warmth and genuineness disarmed me and I felt an instant camaraderie with this man. I told him the truth. “Habana Libre.”

“How much are you paying there?” he asked.

“$85 a night George.”

George had an idea. “Why don’t you stay in a private house, a casa particular, have your own room and only pay $25 a day.  You don’t have to worry. You can bring as many girls to your room as you like.”

“That sounds like a good idea George,” I said.

George smiled. “I can bring you there and show you the room now if you’d like”

“I’m busy today,” I said. “But I can see it tomorrow if that’s okay.

“See you tomorrow,” said George.

We shook hands and promised to meet at noon the following day. Same time, same place. As I started walking away George shouted, “Danny, is that 12 o’clock American time or Cuban Time?”

I yelled back “American!” He laughed and gave me a wave.  George was still standing on the side of the Plaza when I flagged down a taxi and was probably still standing there when I reached the Habana Libre.

I went straight upstairs, took a quick shower and decided to go down to the lobby for a drink before I went out on the town. I sat down in the atrium and ordered a Cuba Libre from Rudy. Rudy always looked professional in his burgundy vest, bow tie, and dark pants.

There was so little English spoken at the time that I cherished the opportunity to speak English with a local Habanero. I told Rudy I was from California and he got very excited. He told me he had never met an American before and he was thrilled with the opportunity to speak English with me.

Though Rudy was a short guy, he had the typical dark Latin features. He had been working at the Habana Libre for a couple of years and had never served an American before. It didn’t take long before we got on the subject of martial arts and Rudy told me that he had a black belt in karate.

As a former martial artist myself, I promised Rudy I’d bring him martial arts magazines from California on my next trip. If there was a next trip. I also had some Karate weapons and maybe even a gi that I could bring him as well.

I was sitting at a table near the front door of the atrium and as usual, the first Cuba Libre tasted so good I ordered a second. As I sat there just observing patrons around the lobby two young girls walked in the front door and stood near me looking at a ballet poster propped up near the entrance.

I immediately realized that these two young girls were ballerinas themselves. Their hair was tied back in a tight bun and I could tell by the way they carried themselves that they were dancers. After a few minutes of observing them, I got up, walked over to them, and asked if I could buy them a Coke.

Somehow, with my very limited Spanish, I was able to convince them to come over to my table and join me for a drink. One of the girls was a beautiful blonde, petite with green eyes and the other was a shorter, coffee-colored girl with beautiful blow job lips. The mulatta spoke a little bit of English so we started conversing and got to know each other a little bit.

When they finished their drinks, I asked them to come back in the evening and I would like to take them to dinner at the Hotel Nacional. Surprisingly, they agree. We shook hands and agreed to meet at 5 o’clock in front of Habana Libre. I put the odds of them returning about 40/60 against.

Shortly after 5 o’clock, I was having a casual drink in the lobby bar when I noticed three young girls walking up the driveway. I met them at the front door and the cute little black girl Yenet introduced her older sister Yandra. I was taken aback when Yandra handed me a 4-pack of Montecristo No. 4 cigars.  Along with the blonde ballerina appropriately named Blanca, we strolled down La Rampa to the Hotel National.

The National had a nice, Polynesian-themed restaurant in the backyard that specialized in roasted chicken Pollo Asado and other simple Cuban dishes.  We were seated for dinner and I ordered some drinks.  With my limited Spanish and Yandra’s broken English, we were able to make a bit of a conversation. They were fascinated to meet an American but I only had one thing on my mind.

After dinner, I was a little tipsy so we went to the front of the hotel and jumped into a taxi. I guess I could blame it on being drunk, but I did something next that I would regret later. As the taxi pulled up in front of the Habana Libre, I asked Blanca if she would like to spend the night with me. Yanet and Yandra giggle thinking I was jesting. I told Blanca I would give her some dinero in the morning to take home to her family.

Naturally, she leaped out of the taxi. I gave a half-hearted wave to the sisters and walked into the hotel behind Blanca.  Unfortunately, I would never see the sisters again… They treated me very respectfully, so it was a bad move to take their friend for the night, but at the time, I was burning up with “Cuban Fever.”

Blanca was truly a beautiful young girl. With her natural blonde hair and aqua-blue eyes, she may have been of Russian descent considering Russians have integrated into the culture since the beginning of the revolution.

I could tell from her body language Blanca was feeling a little uncomfortable. I assured her that I would just like to spend the night with her, and she wasn’t under any pressure to perform.

I explained to her the only way to get up to my room without getting nabbed by security was the ol’ fire escape trick.

There I was again, on the 12^th floor looking down the escape and seeing a tiny hand on the railing winding up the staircase. It was like a mirage seeing this beautiful, young ballerina, tiptoeing out of the stairway and into my room.

She was very delicate, quiet, and a bit shy.  I was very passionate with her as we shared a wonderful night of gentle lovemaking.  We were up at first light and I could sense she was anxious to go home. As she was leaving, I handed her $30 and watched her tiptoe down the hallway and into the fire escape.

I imagined her tiptoeing through the bustling, spacious lobby of the once-famous Havana Hilton Hotel, through the crowded lobby full of horny tourists and disappearing into the morning sun of Havana. I had netted another fish last night, but I should have thrown this one back, into the cesspool of life here, where there’s no chance of escape from a failed revolution.

I took a shower and went down to the lobby to have a sandwich. I didn’t linger because I had an appointment with a tall Afro-Cuban with pure white hair named George at noon “American time.”  I ordered another beer for the road, went out the front door into the beautiful Cuban sunlight, and yelled “Prado.” An 80s yellow Lada pulled up with a smoking tailpipe and I jumped inside.

The post Chapter Three appeared first on The Cigar Diary.

The next day I got up late and went straight to the retail store and bought a 4-pack of Montecristo No. 2 Cigars and sauntered out to the back patio for a drink. Down the sidewalk near the edge of the bluff, a booze cart was parked next to the cannon placements from yesteryear. The area was nicely groomed with tables and wooden benches to view the royal blue Gulf of Mexico across the street. Ivan the bartender stirred me up a Cuba Libre and I sat on the bench with a stogie and planned my next move.

Down on the Malecon, it appears that the regular means of transportation for the average Cuban these days is the bicycle. Ivan looking every inch a bartender from the 1950s in his starched white shirt, black pants, and burgundy vest told me the government bought a million bicycles from China and distributed them to the Cuban people to help them deal with the pressures of the “Special Period.” There are very few new cars on the streets. Mostly originals from the 1940s and 50s. The only new vehicles seem to be government-owned tourist taxis and buses with HabanaTour printed on the side.

For bar hopping around the city, there are bicycle rickshaws available that can peddle two people short distances. It amazes me that Cubans have been able to tolerate this dire situation for so long. When the country was supported by the Soviet Union it was livable for those who worked for the state and had access to pesos and monthly rations.

In the afternoon I made my way upstairs to the bar and billiard room.  The bartender who worked the room was Israel. Neatly dressed in his starched white shirt, black pants and vest; he carried himself like a seasoned barkeep although he couldn’t have been a day over 25. He spoke perfect English and made delicious margaritas. I found it interesting that drinks were only three dollars in a five-star hotel and three dollars in dive bars around town, but I wasn’t complaining.

Considering I only brought about eight hundred dollars in cash, I went to the lobby to see if I could get money off my Gold credit card.  It didn’t take long for me to realize that there was no way to get money off of credit cards if they were issued by a U.S. bank. The first glitch of the trip. I would need to call my brother David and convince him to wire me money.

The next day, I made the dreaded call. He agreed to send me one-thousand dollars but it turned into a fiasco. David had to send the money to an office in old Havana called the Assistir office. Sending money from California, it had to go first to an international bank in New York, where of course they took a fee, and then to Montreal Canada, another fee, etc.

After several days, the bank in Canada would send the money to Havana and once it arrived there, the Assister office would take their fee as well. Out of the $1,000 he sent, only $820 arrived in Havana for pickup. But I was thrilled to be solvent again. Havana quickly turns from paradise to hell when your money runs out.

I went down to the office on El Prado and picked up the money which offered me a lot of new opportunities. After a nap and shower, we went out to the backyard of the hotel and had a Cubano sandwich and billed it to my room. Then took a walk down to La Rampa to see what was what.

As soon as we got to the corner two girls approached me. One of the girls was a petite blonde who introduced herself as Marga and her friend was a cute coffee-colored Mulatta girl named Nelsie. I was immediately attracted to Nelsie with her stunning smile, bright eyes, and thick black hair tied back into a short ponytail.

I invited them back to the hotel. “imposible,” said Nelsie, reminding me that Cubans were not allowed into hotel rooms. They said they would come back at nine o’clock and they knew someone who worked at the hotel who could sneak them upstairs. We kissed and they said “hasta luego.”

Around 8:00 pm I went to the video room, had a couple of drinks then headed up and took a shower. After I shit, showered and shaved I walked down the driveway at exactly 9 o’clock to see two beautiful young girls standing before me. They were dressed up like they were going to a presidential ball, which kind of stunned me a bit. Nelsie was wearing a flowing red dress and oversized heels that I didn’t particularly like.

It was obvious Nelsie was trying to make herself look older for me but it negated her natural teenage beauty. It made her look like a hooker in her mid-20s. Nelsie told me to go to the front of the hotel and ask for Oscar. She knew him from her barrio in Old Havana and said he would escort her and her friend up to my room on the 7^th floor.

Sure enough. I found the tall, Russian-looking Oscar and he told me to repeat the same routine as the night before. He said there are two rules, “I know,” I replied.  “I have to pay $60 and the girls have to be out of the hotel by 5:45 am before his shift ends.” Then I decided I’d just spend the night with Nelsie. I could catch up with Blondie down the road sometime.

Well, it was déjà vu all over again. Like before, the room was dark and no sooner was Nelsie in the door that she sultrily removed their red dress, letting it drop to the floor, and slowly crawled onto the bed wearing only her underwear. Cuban girls don’t leave much to the imagination. She put her head on the pillow, took her bra off and lay there in her little white panties that almost glowed against her dark skin. I could see her large erect nipples standing up in the shallow light.

Her firm breasts stood up from her chest and her areola’s were swollen with erect nipples on top, long and hard, just as I like them. From the side, they looked like little chocolate ice cream cones with cherries on top. Considering I couldn’t have a conversation with her, I just leaned over and started sucking on them.

I slid my hand underneath the elastic band of her panties and brought my middle finger to rest in the crack of her pussy. As we kissed, I began to softly stroke her little twat in an up-and-down motion. With each stroke, I pushed my middle finger deeper into her cunt. She placed her right hand over mine and pressed down as she began to squirm, wiggle and hump. I had her just where I wanted her.

Before long, Nelsie had her legs spread and knees raised in an inviting posture.  I pulled her under me and got on top like an Olympic wrestler and I pushed myself inside of her tight little pussy. When she wrapped her arms and legs around me our souls melted together in a rhythmic copulation of ecstasy.

I fell into a kind of euphoric dream world where pain and sorrow didn’t exist, only happiness and joy. We became one body, neither male nor female in a squirming motion of ecstasy and love. Our perfect union was shattered by the loud ringing of a phone.  Moments later there was the echoing sound of knocking on the door. It was Oscar calling us home from Shangri-la.

I motioned to Nelsie to get dressed quickly and to buy a few more minutes, I opened the door a crack and handed Oscar three twenty-dollar bills.  From my limp shirt pocket on the floor, I pulled another $20 and tucked it in Nelsie’s hand. We agreed to meet later in the evening and she slipped out the door. Another night in the city of sin I thought to myself.  Alone again, I felt a kind of sadness. This place is like a giant bordello mixed with sadness and joy.

The following morning, I was up and at’em by nine. After a Cappuccino on the patio, I made my way up to the cigar store on the second floor to price out some sticks. It was a very small room but they had a large and varied selection of cigars. Montecristo No. 2., Partagas Serie D #2, Cohiba Robustos, Ramon Allones Specially Selected and they even had the hard-to-find Hoyo de Monterrey Double Corona’s.

The prices ranged from 160 dollars on up with Cohiba being the most expensive. Now that I had the price range, I knew I had to keep aside at least $400 for cigar buying. Cuban cigars would make a nice gift for certain friends and I’m sure that no one I know has ever tried an authentic Cuban cigar. After about an hour at the pool, I went up for a nap before dinner.

I started the evening at the video bar. My boy Ivan was working the night shift so I sat down and ordered a Cuba Libre. The room was dark with the only light coming from the TV mounted on the wall in the corner of the room.  Oddly, a Cuban girl was sitting at the end of the bar chatting with Ivan.

After several glances in my direction, Ivan came down and asked if I wanted another drink and told me that the girl sitting in the dark asked if I would buy her a drink. “Sure, why not,” I said and lifted my glass in her direction. She smiled and waved.

The next thing I knew the mystery girl was sitting next to me. “Well, here I go again’” I whispered to myself. She offered me her hand and said “Angela.” “De donde eres?” she asked. “Estados Unidos,” I replied and her eyes lit up. “Wow!”  For an instant, I bet this broad envisioned herself living in a big house in Florida with a pool and a new car in the garage.

She had an elegant beauty to her almost a classy look. Dark eyes with thick shoulder-length hair. Her skin was white, almost alabaster, with lips painted red to draw attention from a deep scar above her right eye. Maybe she worked in the food service business considering she was still attired in her white blouse, navy skirt, and black pumps.

After a few minutes of small, and I mean “small talk,” she took my hand and walked me to a booth in the dark corner of the room. We started softly kissing and I wrapped my arm around her neck and the other I slid into her blouse and began to massage her soft white breasts and hard nipples. After fondling them for a few minutes, she gradually worked her hands between my legs and started rubbing my rock-hard erection through my pants.

She unzipped my fly and my prick popped like it was on a hydraulic spring. Angela didn’t waste a second and grabbed ahold of “Junior” and began a nice, even, up-and-down stroke on him, with her tongue still buried deep in my mouth. The scene was indescribably graceful and erotic.

She continued to softly jerk me as I kept one eye on her and the other eye on our mutual friend, Ivan the bartender.  I didn’t have to worry about her picking my pockets.  I left my wallet in the room and my twenty spot was buried deep in my front pocket.

I leaned my head back on the booth and she just kept stroking it nice and easy. I slouched down a little so our impassioned kissing would not be interrupted. Suddenly I had to blast and I turned toward her in time to shoot my load over her bare legs and across the front of the naugahyde booth. Angela jumped up and went to the bar for napkins.

Since Cubans are not allowed into a hotel unaccompanied, this girl after all could very well be Ivan’s girlfriend or even his wife. Who the fuck knows? The putz could have brought her into the bar tonight to make a few extra bucks for the family. And if she’s just a friend, he gets a commission. Either way, he wins.

She cleaned up the mess and we made our way back to the bar in the same two seats where this whole thing started. Lucky for us, no other guests had come into the video room. But it was so fucking dark in there, they probably wouldn’t have noticed us anyway.

There was a rack of candy bars behind the bar and I called Ivan over and ordered us another round of drinks and a large candy bar for the senorita. After I paid the bill and tipped Ivan, all I had left was a sawbuck so I handed it to the dame. She immediately started whining about a hija at home and money for a taxi bla, bla bla. I told her I’d have to go upstairs to my room and grab more cash.

I finished my Cuba Libre, kissed Angela on the cheek and told her I’d be back in a few minutes. Her eyes followed me to the elevator directly across the hall.  I went up to the seventh floor and walked into my air-conditioned room at the end of the long hall. “Fuck it,” I thought. I peeled off my clothes and lay on the bed with the soft humming of the air conditioner filling the room. “Another crazy night in Salsa town,” I said to myself and turned off the light.

My two weeks were winding down and I only had two days to figure out how to pay the hotel bill. And it wasn’t just the room bill that worried me, but the tab for all of the meals, drinks, and incidentals I charged to the room. I made my way to the front desk and asked for a subtotal of the bill.

When the printer finally stopped spitting out pages, they handed me the total in a manilla folder. I looked down at the invoice and immediately back at the front desk where the entire staff was standing and looking in my direction.

I went out to the patio, ordered a cappuccino and sat down to peruse the bill. My only hope was my unused Gold Mastercard I kept for emergencies. But it was a Mastercard and they don’t take American Mastercard but I had to try. The only other option was to call home for more money.

The following afternoon, I went to the front desk and told the girl I’d like to pay my bill for room 714 and nonchalantly handed her my Gold Mastercard.   “I’m sorry senor,” she said, “but we don’t take credit cards drawn off of American banks because of your embargo”. She could see the fear and desperation in my eyes.

I stood there wishing I could be instantly transported to an island a million miles away or magically transform into one of the rich foreign tourists that were piling through the front door, flush with cash and useable credit cards psyched up for a week of fun in the sun.

I thought about calling my brother again but knew that he wouldn’t like it and the aggravation wouldn’t be worth the call. Probably easier to go to jail for five years in Cuba than deal with the drama. The front desk sensed that I was worried and kept their eyes on me as I paced back and forth across the lobby.

I thought about my options. I could make a mad dash to the airport and try to get out of the country before they knew I was missing, but that was a big risk. If I were caught, I’d be thrown in jail, for who knows how long.

With very few options available to me, I waited about thirty minutes and went back to the desk and asked for the manager. Several minutes later a beautifully manicured Latina woman walked up to me and asked if I needed help. I explained my dilemma. “My first time in Cuba and I did not know the hotel didn’t accept American credit cards. “I know it’s because of the stupid embargo that the United States has imposed on this poor country for so many years,” I said.

She miraculously asked for the Gold Card once again and told me to sit down in the lobby and wait. She disappeared into the back office. I sat there nervously for about thirty minutes until she returned… with a receipt for me to sign. Somehow, someway, she made it work. I grasped her hand and said, “Mucho, mucho gracias”! I gasped a sigh of relief. For the final two days of my trip, I could pay with the cash I had left from the money transfer

With only two days left on my trip, I needed to get serious the last few days and take care of my cigar business. Unfortunately, I had to cut Nelsie loose to get it done. I had plans to meet her and her friend at noon and it was already 1:15 when I made my way to the end of the long driveway to see if they were still waiting. As soon as we reached the street I saw them sitting on the steps of an apartment building.

They ran across the street and Nelsie and I embraced.  I took her hand and the three of us walked down to the Malecon. We sat on the sea wall and I did my best to converse with them. Nelsie was a sweet girl and I wouldn’t mind seeing her again if I ever came back to Havana.

I handed Nelsie a $20 bill and reluctantly gave Blondie a 10 spot. As they took the money they kissed me on the cheek. Nelsie gave me her address written on a paper bag with a black eye brow pencil.  Although I didn’t believe it, I said I would be back proxima mes (next month). We hugged a final time and they sadly walked away.

I watched as made their way down the Malecon, their fragile frames growing smaller and smaller until finally fading into dark specs on the horizon. The blue-black sea shot a burst of white mist high into the air as I crossed the street to the Hotel Nacional de Cuba sitting high upon the bluff.

The following day I left the country the same way I entered it, but the exit was a bit unusual. After clearing immigration, I had to clear customs.  I had nothing to declare. My only purchases were two boxes Romeo Y Julieta cigars that I checked in my suitcase. After clearing, I went to the retail store and bought a bottle of Havana Club Reserva Rum and sat down at my gate thinking about Nelsie and her beautiful brown tits.

I knew that my life had changed forever and in so many ways, but I also knew I wouldn’t completely understand it I got home and had a chance to process it all. Havana Cuba was my new fantasy island and it offered everything a man could want. But it could ruin a man just as well. But maybe I needed a little ruining and there wasn’t a better to do it.

#cohiba #cubancigars #sexcuba #cigars #cubacigar

The post Chapter Two appeared first on The Cigar Diary.

Spring 1994

My first venture into Latin culture was during the production of a documentary I shot in Central America in the early 1990s. The production’s itinerary took us to Costa Rica, Nicaragua and Panama.  Almost immediately I resonated with the people, the music, the food and of course hot Latino women.

Several months after the show was wrapped, I was sitting in our production offices on Wilshire Blvd. when the set designer stopped by for a chat. Glenn recognized that I had connected with Latin culture and suggested I add Cuba to my bucket list.

Naturally, my immediate response was “Cuba? We can’t go to Cuba.”  “Sure, you can,” said Glenn. “You can’t fly direct from the states but you can depart and return from Mexico.”  I didn’t know much about Cuba other than it still had a Communist government and considering the longstanding trade embargo the US had on Cuba, the travel ban for US citizens remained in full force and would remain so as long Fidel Castro ran the show

But the seed that Glenn had planted that day piqued my curiosity and adventurous spirit. For weeks it had me thinking seriously about making the trip to the mysterious, forbidden island.  At that time, I had never known anyone who had been to Cuba or anyone who had even considered going there because of the stigma.

There was an unjustified belief that Americans were hated by the Cuban population and there was even a strong possibility that it could actually be dangerous for U.S. citizens to travel there. Regardless, I had made my decision and for better or for worse, I was going to Cuba.

I submitted my Visa applications to the embassy of Switzerland in Washington, D.C. After a two-week turnaround, it finally showed up and I immediately drove down to Tijuana, Mexico to purchase my airline tickets.  I found the Viajes Montfort SA agency on Revolution Blvd. and booked my trip for March 20, 1994.

When the day finally arrived, I departed from Los Angeles and landed in Mexico City four hours later for an overnight stay. The Sheridan Hotel was across the street from the city’s international airport. The following morning, I boarded a 10:30 am flight on AeroMexico Airlines for my 3-hour flight to Havana.

The majority of passengers on the flight were Cuban exiles returning home with food and medicine for family members. Landing in the Cuban capital was a unique experience. Jose Marti International Airport was a two-story structure that was painted in a drab gray and green and looked like something that was Soviet-inspired.

I disembarked the plane down a portable staircase, past two Cuban airport personnel dressed in green army fatiques and brandishing automatic weapons. Passengers scampered across the tarmac to the immigration and customs building. Not speaking a word of Spanish made my interrogation to enter the country an interesting experience.

Immigration was a slow, cautious process on behalf of the military staff. They ran a background check on me and finally after ten minutes or so, I heard a heavy stamp hit my passport and visa. They left a weird stamp in my passport that looked like a smoking jenie lamp. The door buzzed open and the jefe motioned with his head for me to go through it to the baggage claim area.

After my carry-on bags were x-rayed and I was body scanned, I continued to the baggage carousel to retrieve my suitcases. It’s usually takes a few minutes for the bags to come out because every suitcase entering Cuba is x-rayed for anything that could disrupt the revolution. When my bags finally spilled out, I grabbed them, showed a customs agent my declaration form and went out the tinted sliding door.  I jumped into the first taxi I saw and said, “Hotel Nacional por favor.”

Jose Marti airport is located about 15 km from the center of town in an area called Rancho Boyeros. Driving into town we passed fields and farmland and what seemed to stretch for miles in every direction.  My taxi driver was beside himself when I told him I was from the U.S. He stared at me through his rear mirror as if I were a green Martian from outer space.

The Hotel Nacional de Cuba was about a 30-minute drive from the airport and sat on a bluff overlooking the famous seaside Malecon Boulevard. It’s located in the business district of the city called Vedado. The hotel was built in 1930 and is considered the crown jewel of hotels in Havana.

We pulled up in front and walked up the red-carpeted steps and checked into the hotel.  They put me on the seventh floor. (It wasn’t until much later that I discovered all Americans who visit Havana are put on the seventh floor where their phone calls are monitored).

From my window, I had a nice view of the Malecon that runs from Old Havana to Miramar.  After a quick shower, I went downstairs and began to explore the grounds of the hotel. The back patio area with its finely manicured yard was one of the best features of the place.  There were comfortable couches and coffee tables and the sounds of a trio singing Latin love songs.

I ordered Cuba Libre, the popular Cuban drink of rum and coke and felt the balmy breezes blowing in off the gulf. After an hour or so and several more Libre’s, I ventured down the long driveway of the hotel for a walk around the block.

Growing up in a racially divided country, it was a little intimidating seeing mostly black guys hanging around the parameter of the hotel trying to make conversation with tourists. I tried to override my racist conditioning from the States and be as trusting and cordial as possible.

It was a good lesson about being judgmental. Still green, I wasn’t sure if the hotel was in a “bad” neighborhood so I proceeded with caution. (We would come to find out, there are no bad neighborhoods in communist Cuba. They’re all bad but very little violent crime. One of the goals of the Cuban Revolution was the creation of a classless sociality with equality for everyone, regardless of race).

It took a few days to get acclimated to the culture shock of even being in a Communist country that hadn’t changed much in almost 40 years. Fidel Castro and his brother Raul have been in power since 1959. I knew intuitively politics was something you didn’t want to openly discuss in Cuba.

One block east of the hotel is 23^rd Street, known as La Rampa (the ramp). It descends in a downward slant from the famous Cappelia ice cream park and spills out on the Malecon Blvd. Just a casual walk down La Rampa drew the attention of several girls who approached me trying to initiate conversation but I ignored them.

After a day or two of wandering around Vedado, I felt comfortable enough to venture in a taxi to old Havana to have dinner. I went to one of Ernest Hemingway’s favorite watering holes the El Floridita, home of the daiquiri. After dinner, still hesitant to explore on foot, I cabbed it back to the hotel.

There were chica’s everywhere in Havana. Girls took to the streets when the government made it legal for Cubans to possess American dollars. Before 1993, if a Cuban got caught with American currency, they went to jail for as many years as the demonination they were caught with. Having dollars makes it easy for me.

When I arrived at the Nacional. I saw a couple of girls sitting on shaded steps that leads to the hotel pool. They stared at me as we passed and smiled and as I casually waved the girls giggled.

Once I got inside the hotel, I thought to myself, what the fuck. I’m going back outside to see if I can somehow get one or both girls up to our room. Sure enough, I sat down beside them and tried my best to initiate some kind of conversation.

We chatted for a few minutes and quickly realized they were willing to sell themselves.  They claimed to be sisters, but were shabbily dressed and obviously not pros.  This particular time, the early 1990s in Cuba called the “Special Period.” It was the best of times for tourists and the worse of times, economically, for the Cuban people since the Castro revolution began thirty-five years earlier.

Once they agreed to come up to my room, I hatched a plan. I went into the hotel and I found “my guy” with a bright smile named German who worked the night shift at the front desk.  I told him I had a couple of girls outside and I’d like to bring them upstairs. He told us to go to my room and he would arrange to get them there.  “But there are three of us on the shift,” he said.  So it’s going to cost you $20 each.

Sixty bucks to have these young lovelies delivered to my room? Let’s do it!  I jumped in the elevator and went back up to 714 took a quick shower and waited patiently for a knock on my door.  About fifteen minutes later, I heard voices outside my door and opened it slowly Mr. German was standing in the hall with my two seniorities.  As the girls slipped inside the room German whispered, he would come back at the end of his shirt and get the girls out.

The girls sat nonchalantly on the bed and I offered them a drink to break the ice. “Un Cuba Libre?”  They giggled and got up and went into the bathroom together. I made a drink for myself, sat in a large chair and looked out into the night at the street lights running along the Malecon.

The lights were off when they came out of the bathroom with towels wrapped around themselves and climbed into bed. I walked over to the bed and climbed in between them and sat with my back against the backboard of the bed.  They pointed back and forth to each other and said that they were hermanas. (sisters). The older one was Marta and I couldn’t’ understand the younger one’s name. Did it matter?

Marta was quite beautiful with striking dark features, a light olive skin tone and deep dark eyes. His sister was every bit as pretty as Marta. She had luscious, thick black hair that fell to her shoulders. But it was her heavy, black eyebrows that had my attention. I was lost in another world that I never wanted to leave.

In a natural motion, Marta put her head between my legs and began sucking my cock as I put my arms around her sister, pulled her close and we began kissing like a couple of teenagers. It put me in a blissful, indescribable state that seemed to last for hours. Before long, Marta was sitting in my lap, her soft legs wrapped around me, her hard ass rising in an up and down motion that griped me in heavenly waves of pleasure.

When I laid on my back there was just enough light coming through the window that we could see each other’s eyes and have a silent conversation. The hermana just sat there watching us with a detached look on her face like another day on the job.

With my big hands holding her hard round ass, Marta rose up and down on my cock, soft moans emanating from her gentle lips. I thought it would have been a faux pas to move on her younger sister so I let it pass. But this was Havana in the early 90s, maybe this was Havana anytime and here in the tropics right or wrong, good and bad is often forgiven and muddled into the need for survival.

When Marta and I finished, we lay there, all three of us watching the blades of the Casablanca fan hum and whirl about our heads. Where was I? Was this happening to me I thought. It was early morning now and the night shift was about to end. This dream had to end sometime.

I gave Marta 20 dollars and little sis ten bucks for getting into bed with me and letting me kiss her and play with her pussy.  As they got up and walked to the bathroom and I picked up the phone and called the front desk.  “OK German, get these little bitches the fuck out of here. Mañana es otro dia.

A few minutes later I heard a soft knock and I could see dark shadows swirling under my door. German was waiting on the other side and whispered Vamos! As the girls walked out of my room, they kissed me on the cheek and followed German down the hallway never looking back. I went over to the table and poured myself a Cuba Libre and looked out on the Malecon. As the morning workers peddled their bicycles along the ocean boulevard, I watched the sky transition from deep blue and indigo to orange, pink and gold. I raised my glass. “Buenos Dias Havana!”

The post Chapter One appeared first on The Cigar Diary.