Havana, Cuba – PART 2

Alesia My Guide

I found myself in Mexico City with my partner in crime Alesia. As had been the custom for many years I arrived early for my business meetings and spent time with her before we had to flip the switch and become professionals. This particular trip we were both preparing to head over to the office on the Reforma as my mobile rang, and I was informed that the meetings for the week had been canceled. Several folks in the office had become sick and thought it best to wait until next month. What to do crossed our minds? We found a place to have a light breakfast and discussed our options. Was it better for me to return back stateside? Alesia always wanted to visit Havana, but did not really have the means. She knew that I had family there and blurted out “Vamos a Habana!”. I was hesitant at first, but after thinking it through it sounded like an excellent idea. Having family there meant I simply had to fill out some simple forms at the embassy and as a Mexican citizen, she had no restrictions. As we sat there drinking our coffee, we went about all of the preparation and reservations, and in less than an hour we were set. The US Embassy was only a couple of blocks away on the Reforma, so I stopped there and completed the necessary forms and obtained the approvals. Two days later, we would be on our way.

"Cuba!" she whispered, clutching her worn leather backpack. "We're actually going." Watching the sprawling, smog-hazed expanse of the world’s most populous city shrink beneath the wing was a moment of quiet reflection. Soon, the dry landscape gave way to the endless, dazzling blue of the Gulf. We spent the short flight reviewing our travel documents, sharing headphones for a playlist heavy on salsa music, and exchanging glances that spoke volumes about the adventure ahead. As the plane began its final descent, the landscape transformed. The turquoise shallows of the Caribbean appeared, and then, a patchwork of vibrant green land leading up to the sea-battered coastline. The moment the cabin door hissed open in Havana, a thick, humid air—heavy with the scent of jet fuel, sea salt, and something indefinably tropical—enveloped us. The airport itself felt like stepping onto a movie set decades ago. Everything was functional but dated, the lighting fluorescent and harsh. Customs was a slow, deliberate process. The officer was stern, barely making eye contact as he inspected our documents under the cold light. Alesia tried a cheerful "Hola!" which was met with a practiced, neutral expression. Finally, the heavy, official thud of the stamp on our passports was the sound of true arrival. We had made it.

Outside, the scene was a dizzying kaleidoscope. Forget the sleek Uber queue; impossibly vibrant 1950s American cars were everywhere. We chose a faded cherry-red Chevy Bel Air—its interior cracked vinyl and its engine rumbling like a distant thunderstorm—and were instantly charmed by its owner and driver, Isadora. She was a striking, middle-aged woman, immediately standing apart from the crowds with a beauty that spoke of her heritage. Isadora carried the angular symmetry of her Russian father—a scientist, posted there decades ago—combined with the undeniable, sun-kissed warmth of her Cuban mother. Her skin was a beautiful, smooth olive tone, deeply tanned across the high planes of her cheeks. Her body was full and confident, fitting snugly behind the large steering wheel, and her breasts rested against the thin cotton of her simple white blouse with a proud, matronly curve that drew the eye but demanded respect. But it was her eyes that truly arrested us. They were an extraordinary shade of pale, glacial blue, utterly uncommon in Cuba, and set beneath dark, perfectly arched brows. They seemed to catch and refract the harsh tropical light, giving her gaze a penetrating, almost startling clarity. Her hair was a thick, dark braid, pulled severely back and secured at the nape of her neck, emphasizing her sharp cheekbones and the strong, determined set of her jaw.

"Bienvenido a la Habana," Isadora announced, her voice a low, gravelly alto that made the Spanish sound even more musical. As she expertly guided the massive, ancient car through the traffic—one hand draped casually over the worn steering wheel—she became our impromptu historian. She spoke of the city's past not from a textbook, but from memory and observation. She pointed out the Soviet-era apartments, describing how they were symbols of a forgotten promise, then gestured toward the crumbling Spanish forts, explaining how the salt air was slowly dissolving history itself. Every cracked building facade and every blossoming flamboyant tree came with a story, filtered through her unique, dual perspective. She narrated the drive into the city with a proud, melancholy air, making us understand instantly that Havana was not just a destination, but a character—flawed, magnificent, and utterly unforgettable and very sexual. The drive into the city was a sensory overload of palm trees, dilapidated Soviet-era apartment blocks, and the shocking sight of old, stately colonial homes decaying gracefully in the relentless sun. Our hotel, a grand old dame in Habana Vieja, was a triumph of peeling grandeur and high ceilings. The drive ended, and we were left with the scent of old leather, gasoline, and Isadora's quiet certainty ringing in our ears as we stepped out onto the cobblestones of Old Havana. Before she left Isadora scribbled her telephone number on a piece of paper in case we required the services of a driver throughout our four days there. She preferred to be paid in US dollars. We paid her, tipping her handsomely and telling her, “Seguro” certain we would likely need a driver at some point.

After dropping our bags, we couldn't wait another minute. Stepping out onto the cobblestones of Old Havana was like entering a living, breathing museum. The scenery was intensely, intoxicatingly beautiful. The streets were narrow, creating cool, shaded canyons that offered respite from the tropical sun. The air was a rich mix of aromas: pungent exhaust from the classic cars, the sweet smoke of hand-rolled Cuban cigars drifting from doorways, and the salty freshness of the sea, which was never far. Alesia stopped dead in her tracks, pointing at a group of old men playing dominoes on an overturned crate, their faces etched with decades of Havana sun and laughter. She took a deep breath. "This," she said, her voice filled with awe, "is exactly what I imagined. More, even." She was aroused at the sight of it all, as was I at the amusement in her eyes and her arousal. We returned to the hotel and rinsed off in the shower in an effort to remove the sweat of the day and soon we were in bed working up more sweat. The city was already having its effect on us.

Later that evening, after the fierce heat of the day had ceded to a balmy night, we descended a narrow, velvet-roped staircase into the hotel’s jazz club. The atmosphere was immediate and immersive—a world away from the bright streets above. It was dark, intimate, and steeped in history. The walls were lined with dark, rich mahogany, and the lighting came only from tiny, focused spotlights illuminating the small, raised stage, and the small amber lamps on each tiny table. A haze of cigarette and cigar smoke hung low, catching the light like liquid gold. I asked the waiter to bring me a Monte Cristo, number two cigar and a Cafecito with a side chaser of seven-year-old Havana Club Anejo Rum as my after dinner treat. We both settled into a pair of plush, red-velvet chairs near the back, Alesia enjoying her perfect Cuba Libre. On stage, a trio was in full swing: a pianist whose eyes were closed in concentration, a quiet bassist laying down a hypnotic, walking rhythm, and a trumpet player, a man with silver hair and a lifetime in his lungs. The sound was liquid and soulful—a perfect marriage of American jazz and Cuban descarga music. The music wasn't just listened to; it was felt, vibrating through the wooden floor, up through our chairs, and settling deep in the chest. Alesia leaned in, her voice barely a whisper over the swell of the brass. "No cell phones, no flashing lights," she said, "Just music. Just… now." We spent the next two hours simply existing and letting the rhythms of Old Havana finally wash over us.

We arrived in our room and immediately began passionately, kissing, and removing our clothes. In an instant, we were completely naked and the minimal air-conditioning in the room was no match for the heat we were generating. I pushed back for a moment and walk toward the French door, which led to our balcony and opened it. The balcony was not very large. It had barely enough room for two small chairs and a very small table. In an instant, I pulled Alessia over and we were both now framed in the doorway totally naked. My hands wandering all over her body, her breasts in the open for all to admire. She dropped to her knees and took my cock in her mouth and began her masterful work on it. I didn't want to cum so I lifted her up and kissed her. As our kiss broke, I sat her down on one of the rickety little chairs on the balcony and began caressing her clit. It did not take very long before her moans of passion where echoing through the street. Neither one of us paid any attention to anybody who could’ve been watching, but were unbelievably aroused at the prospect that everybody could be watching. All of that was irrelevant and when she came she announced it for all Havana to know. The echo seemed to go on for some time.

I took my fingers, fresh with the sweetness from inside her, and placed them in her mouth for her to enjoy. She stood up and placed her arms across the top of the railing and rested her breasts on top of them. Her head over the edge of the railing, looking down onto the street. She looked back at me and begged me to give her what she enjoyed and in short order, I was easing my cock into her ass. For every movement forward, she responded with an equal push backwards to take it in as deep as it would go. Once she was comfortable, I began thrusting powerfully in and out of her, as she took her fingers and massaged her pussy and her clit at the same time. It was after 3am and nobody cared but it all offered her intense arousal and freedom. The moment for both of us arrived almost without warning and we both came exquisitely. We held there for some time. Her looking back, a vision fulfilled and me, gazing deeply into her eyes and both looking at the cityscape all around us that brought this moment. As I began to get soft, I eased myself out of her, she rose, turned to me, and we began a series of long passionate kisses, which eventually lead us to the shower and then to the bed. Sleep came quickly and refreshed us.

The morning sun, filtered through the tall, arched windows of our hotel room and was already hot. The lingering air conditioning kept the space somewhat cool and quiet. We rose at 9 AM after a short night of deep sleep. We ordered a typical Cuban breakfast to the room. When it arrived, the scent of strong, Cafecito, warm, buttered toast, and fresh tropical fruit filled the room. We ate slowly, sitting on the balcony overlooking a narrow, bustling street in Old Havana, watching the city we had as witness the night before awakening below us. As we sipped our coffee and reviewed the worn, handwritten map Alesia had brought, we pondered the day's adventure. Havana was enormous, and the possibilities were endless—the Malecón, the museums, the squares. "We need a break from the crowds," she murmured, leaning back with a sigh of satisfaction. "Something authentic. Something… Hemingway." The word "Hemingway" sparked an idea instantly. The American writer was as much a part of Cuba as the rum. "I know just the place," I said, snapping my fingers. "The place where he kept his boat, the Pilar." It occurred to us immediately: we needed a driver. Not just any driver, but one with stories and the perfect classic car. "Isadora," Alesia said. "She’s the one. She can tell us everything on the way." We retrieved the slip of paper where she had scribbled her number, placed the call, and after a couple of rings, Isadora's low, unmistakable voice answered. She agreed instantly, her cheerful voice cutting through the faint static of the Cuban phone line. She told us to meet her downstairs in an hour, and we quickly dressed, eager to see her brilliant blue eyes and her cherry-red Bel Air once more. Our destination: Cojimar, the small, rustic fishing village that inspired The Old Man and the Sea.

Soon we were on our way…

Images as imagined, from the Internet