This is the first in a series of true stories of sexual adventures I've had over the last sixteen years travelling to the real Cuba, not the all-inclusive, tourist Cuba. Each episode will have first some information about the hookup culture which is so unique in Cuba followed by a hot session with a sexy Cuban girl or woman. If you want to jump to the sex, go ahead but do return to learn more about how things work in that strange island just seventy miles off the coast of Florida but still living like it 1965.
What I write is all true. Well, let's say the situations and broad strokes true but in the fog of lust my memory may enhance some details. I was keeping a diary and my notes in it were written the same night or the next day after great encounters so they should be pretty accurate.
Let me be your sex travel guide of Cuban customs by sharing my experiences as a rather ordinary, American guy who stumbled onto this lusty man's paradise. Future episodes will be 98% sex with occasional sexual travel guide tips as situations arise. But in this first piece, it's important to give you the background so you can better understand what's happening and why.
I am now in 2016, 56 years old. I first came to Cuba in 2000 after a fifteen year marriage ended in an amicable divorce. I was forty, starting my midlife crisis and looking for fun. I'm a successful self-employed person in the tech industry. I had been all in my head since university and wanted more sensual adventures. My career situation gave me lots of flexibility to travel and money to afford it.
I'm pretty fit and good enough looking to have a nice looking wife back in Chicago. I've never had a problem being with attractive women. I love sex and am blessed with the best orgasms in the world. The women I fuck are envious and tell me my orgasm is the best they have ever seen. This is likely why I'm so addicted to sex. A heroin addict couldn't get more pleasure main-lining a hit of heroin that I do cumming. Sometimes the pleasure is so intense, it almost seems death-defying.
I think great sex is healthy and not at all shameful. I believe during sex from the courting, to foreplay, to fucking and post-coitis, men should be the masculine, aggressive and the strong one. Women should be feminine, caring and submissive. That is the way it is in Cuba. These are the natural instincts around sex that have run deep for millions of years and have allowed the homo sapien species to survive. Outside the bedroom, women should have the same pay for the same work and equal rights all around. They have my total respect. I see no conflict in my attitude.
My first trip to Cuba was on a bicycle road trip package tour from Santiago de Cuba, the second largest city. It's located at the eastern tip of the island, far from Havana. It's the real Cuba. The real Cuba is a time-warp back to 1965. The two week travel package gave me one week with the tourist group cycling through the countryside and then a week with a rental car free to roam with a coupon valid for any hotel.
We biked through small towns. I chatted with the Cuban guide and he told me about the Cuban girls, chicas, who were eager to hook up with a tourist. That seemed a much better way to experience Cuba than peddling in the hot sun. I got him to arrange a car to come for me and drive me back early to Santiago to a "casa de renta", Cuban for B&B, that he knew. He told me the hotels I could stay at with my coupon, had restrictions around girls staying in the room. It was my first of many rides in an old 1950's American car kept running miraculously by ingenious mechanics.
That night I visited a bar on a terrace that my Cuban friend told me was a prime place to pick up a Cuban girl a chica as he called them. It had nice Spanish music playing in the background with ten or so small tables for four scattered around a small open dancing area where several attractive young girls were dancing with either other girls or older men.
I went to the bar to order a beer and a pretty young lady in her early twenties dressed in a cute miniskirt came up beside me. She smiled sweetly and asked me something in Spanish that I didn't understand. The bartender spoke some English and told me she wanted a beer and to sit with me. Naturally I said 'Si' one of the few Spanish words I knew at that time.
We went to an empty table, had a few sips and she dragged me up for my first salsa dancing lesson. After a few songs, I sat down but she kept dancing in front of me in an extremely sexy Cuban way. Then she shocked the shit out of me by sitting in my lap and kissing my neck while whispering soft Spanish words of which only "mi amor" sounded familiar.
A future episode will fill you in as to what happened the rest of the night with what I found out was a twenty three year old primary school teacher. Suffice it here to say I found out that there is good sex, there's great sex and then there's Cuban sex. I was Immediately hooked on Cuba , heaven for horny men of adventure.
Let me explain the Cuban culture around sex. It is extremely casual. People have little money so their recreation is dancing, sex and cheap alcohol. It is very common for older Cuban men to be with younger girls. Nobody seems to raise an eyebrow. Many older foreign men have relationships with young Cuban women, build them houses and support their extended families. This is a country where the average monthly wage is fifteen American bucks and a doctor makes forty at the top of the salary pyramid. Look it up in Wikipedia if you don't believe me.
The foreigners who get into longer term relationships are treated like kings (been there, done that) by the family and neighbors. As soon as the foreigner's vacation time is up and leaves, the boyfriend or husband moves back into the casa and life moves on until he has another vacation. Hell, if the house is a big one with a big extended family living there, it may be that one of the brothers or cousins is really the woman's husband who sleeps in a different room while his wife or girlfriend is getting fucked in another by the sugar-daddy foreigner. Nobody in the neighborhood would ever dream of unmasking this deception.
This is so common that I would guess at least ninety percent of foreigner's relationships are like this. In fact, my guess is likely way too low. It's promoted in a family that has a pretty daughter, to attract a rich (in their terms) tourist. It's a big win when one is hooked.
It's easy for us to be smug about families and husband's pimping out their women. I don't think badly about this at all. Life is impossibly hard when wages are so low. It's fine if a Cuban has a family member overseas sending back money but most don't have that luxury.
It's a win-win situation for the foreigners too. They get treated like the kings they aren't back in their home countries with great, attentive young lovers. They just might get a shocker if they make a surprise visit some night and find their wife sleeping with her 'brother' in the foreigner's marital bed.
Short term, sexual hookups with foreigners can happen at any time and place. A Cubana (generic name of a Cuban woman) might never dream of hooking up and who maybe has never even talked with a foreigner, might jump at the chance if she is approached for simple directions to the nearest restaurant. She might have her eyes on a pair of Nikes at the local department store and decide on the spot to get them with a sex date. They have all heard tales from friends and family about crazy rich tourists showering women with money and goodies and only asking for something as simple as normal sex in return. Whenever I'm chatting with a new attractive Cuban woman and I get the feeling she is available, I'll ask her how old she is or if she has tattoos. I don't like tattoos. You'd only ask her age if you needed her not to be underage for sex. If you needed to know about tattoos, you were planning to see her whole body. Either way, she knows you are looking for a sexual hookup. It's up to her to say yes or no. It's amazing how often this has led to a great sexual experience.
Do the math. If a foreigner buys a girl a pair of runners for fifty bucks, that is three month's salary at her job or the equivalent of more than ten thousand dollars in America at our average monthly salary. I would guess that a lot of women in America that look down their noses at Cubanas, would take ten grand to give a blow job and a quick fuck for an hour or two.
Amazing things can happen out if the blue. For example, I once chatted with a cute university student in a small university town who has a flat tire on her bike. I took her and her bike to the repair shop in my rented car and then my room for a crazy sexy fuck (another future episode). She had never talked to a non-Cuban. I found out she always wanted to go to Havana so I said let's go the next day in my rental car. She was overjoyed and said she would ask her mother and come by the next morning if all was okay.
The next morning I got a knock on my door and went out to see my happy smiling chica with her nice looking mother who by the way was certainly younger than me. It turned out she just wanted to meet me before okaying the fuck-weekend with her daughter. She took my hand in hers, kissed it and thanked me profusely, basically for choosing her lucky offspring for my lust. She kissed my cheek and bid me a bon voyage. It made me feel a bit evil to check out her nice ass as she walked away. In a couple of minutes I was balls deep in the student fantasizing about fucking her mother. I'm so bad. I have fucked twin Cuban sisters at once but never a mother daughter. But who knows? It's Cuba!
Before the first fuck story, let me give you a short dictionary of Cuban Spanish language terms. It's a very good idea to learn sufficient Spanish to get around. I took lessons for years after my first visit. But American tutors don't teach the sex-charged words. Here they are.
By the way, my stories I don't have a lot of the dialog spoken since you non-Spanish readers would just get bogged down.
In the following list, I indicate how a word is pronounced not like it's spelled. You will be talking not writing if you travel to Cuba looking to get laid by beautiful women.
Pussy: boy-joe
