Castro, The Pimp

Nikos and Dimitri sure are a pair of wild and crazy guys. At least once a year, the cousins hop a plane from Chicago to Montego Bay, head to the Air Jamaica service desk, and plunk down $200 for the round-trip to Cuba. An hour or so later, it's Hola, la Habana -- no muss, no fuss, and no passport stamp (just an easily discardable Visa card). Sometimes they come via Montreal, sometimes by Cancun, but these fortysomething dudes always make sure to carry some key knick-knacks. On this particular trip its 30 cosmetics kits to hand to the chicks they plan to meet. Let's swing!

Pathetically enough, in a country of endless shortages, makeup kits are currency, an excellent tool for wooing the potential "girlfriends for hire," the entrepreneurs who are so rampant in the capital of Castro's socialist paradise. Known as jineteras (jockeys), they've become a staple of many a song, joke, and movie. They are regular girls, attractive to downright drop-dead stunning, who like all Cubans need U.S. dollars to survive. They're not looking to simply turn tricks so much as to meet a nice foreign man (old and/or fat is no problem) to wine them, dine them, and maybe even marry them and sweep them away from "all this."

I found out on a recent trip what a gorgeous, paradoxical place "all this" really is. The Southern Hemisphere's largest city is for me one of the most beautiful, magical places in the world, its people among the friendliest and most attractive, and most foreign visitors understandably fall head over heels.

I always wanted to go to Cuba. My parents were there on their honeymoon and from their vivid pre-embargo stories, invariably accompanied by a few bars of a tune and a little Bossa Nova demonstration, I imagined it to be a wonderful lively world of romance and salsa dancing; a city of sensuality. Besides, as an adult I find Latin males to be sexy-hot and have enjoyed the rumor that Cuban men reputedly have the largest penis-size of any nation.

Only once have I had an opportunity to test the principle; a Cuban stockbroker in New York with such an enormous penis it made me gasp. This, coupled with the idea of going to Havana and possibly seeing more specimens on location, was an alluring idea, if not my duty as a sex columnist to get to the truth (though honestly I doubted I'd have the courage to take on the undercover job in a Commie country).

I went to Cuba just before the new Millennium as journalists are permitted to go legally. I feared it wouldn't match up to my fantasies but miraculously Cuba retains its sensuality and sexiness despite its dire economic straits. Caught in a time warp, Havana has the feel of a giant movie set. Many people live in crumbling but ornate buildings, ranging in style from Spanish colonial to mid-20th-century art deco, with interior courtyards and palm tree-lined gardens: its romantic squalor right out of a Delacroix painting. Lots of "grannies" -- still-running Chevys and Packards and Caddies from the '40s and '50s, in hues of sun yellow, fiery red and neon blue -- tool along the boulevards and the Malecon, where waves crash against the seawall and send up spectacular sprays.

And now that UNESCO and European countries have been underwriting the restoration of Old Havana, more of the wonder of this quarter's magnificent architecture is emerging each month.

Everything about this city practically oozes drama and romance. The craggy colonial fortresses El Morro and La Cabaña; the atmospheric nooks and crannies of La Bodeguita del Medio, where Papa Hemingway regularly sucked down his mojito cocktails; Vedado's stately Hotel Nacional, built by Meyer Lansky (Lucky Luciano did the Capri, down the street) and patronized by Erroll Flynn and Ava Gardner; even the monumental Columbus Cemetery. I got a delicious, illicit thrill just from the very act of being an American in forbidden Cuba, in a world visually frozen in the Fifties and soaked with history, with people and places we've all heard of: Guantánamo, Bay of Pigs, Che Guevara, Our Man In Havana, El Duque.

And in all my many encounters with the locals, I couldn't help noticing that despite their often trying circumstances, most Cubans have managed to hang on to their friendliness and sense of humor -- not to mention their downright sexiness. No sign here of the sourpusses of Poland and Russia. Instead, there's a thrill and excitement in Havana and a real street energy throughout the day and night, with salsa bands playing in the handsome squares and restaurants of Old Havana. It's a Latin thing, my Cuban-American friend Jorge tells me. Cubans are simply naturally irrepressible.

And did I mention they love visitors? And not just for their wallets and gonads, either. The stupidity of the U.S. embargo in this day and age became crystal clear to me the more I talked with Cubans. Everyone talks openly about how sick they are of Castro and the grubby little system they're trapped in; the only thing that will bring change is more exposure to America and the world, not less.

And individual Americans, at least, are increasingly happy to oblige. We Yanks have supplied the single largest contingent of visitors to Cuba for the past two years (a smug Dutch investment banker living here told me that on its lists of tourist arrivals, the regime lists the U.S. under "other," yet that number far outweighs any other nationality). The embargo, technically policed by the U.S. Treasury Department, doesn't necessarily forbid most Americans to travel to Cuba, only to spend money there. Apart from special categories like Cuban émigrés, journalists, and such, who are exempted from the embargo and are allowed spend up to $100 a day here, most other Americans get in on the sly via Mexico, Canada, Jamaica, or the Bahamas - and virtually no one gets penalized -- fined perhaps and contraband cigars yanked away, but not jailed.

Tourism is now the lifeblood of the Cuban economy, and even though there's a kind of much-resented apartheid that favors foreigners over locals in just about every area imaginable, most Cubans are still glad we're coming on down. Why? Because for them, the economic difficulties that started out with the bloqueo, the 37-year-old U.S. embargo, deteriorated into downright misery after the Soviet Union collapsed in 1989 and cut off its multibillion-dollar annual subsidy.

Since 1994, though, Castro's police state has been pulled from the brink of disaster by investment from Europe and Mexico, but people, as usual, got screwed as the Cuban peso became all but worthless. Instead of "Socialism or death!," the new cry is "Dollars or death!" With most monthly salaries maxing out at the equivalent of $8, grubbing for the currency of the imperialist enemy became essential for survival. If you were lucky enough to work in the tourism industry, you had your tips. But if not, what then?

So as many more foreigners started coming a calling, parts of Havana (especially the Vedado district, with most of the big hotels) and beach resorts like Varadero turned into literal meat markets. Pretty young females -- and not a few males -- flocked in from all over the island and offered themselves everywhere, in front of the hotels, on the grand boulevards and especially on the Malecon, Havana's seven-mile sea wall -- chicas and chicos blatantly propositioning and cat-calling to tourists in a babble of languages until they hit the right one. Sixtysomething farmers from Quebec dandled 14-year-olds on the resort beaches of Playa del Este 45 minutes east of town, and Cuba's capital morphed into the Bangkok of the Caribbean.

Marvels Bruce Cassirer, author of Travel and the Single Male, "There'd be thousands of people on the Malecon. It was like being dropped into a fairytale land: Hundreds of women pawing you and wanting to sleep with you for $10 or $15."

But early in 1999, the régime cracked down, forbidding open solicitation and preventing most average Cubans from entering tourist hotels. You could be arrested for being caught with a tourist, and thousands of women were in fact jailed or shipped back to their provinces. And for a while, it seemed to work, kind of. "The women are scared to death now," Cassirer admits. "You have to make a real effort to meet the nice girls." Jineteras and jineteros are still not that hard to find, but they're far more discreet.

It's a completely fascinating scene, as I found on a recent trip. Milady, a mulata from the eastern city of Holguín, explained that the girls now hang out in certain bars or in nightclubs like Johnny's in Vedado and Casa de la Música in Miramar. Cover charges are steep ($20 isn't unusual), but some can get in on credit; if they find a boyfriend inside, they'll reimburse the doorman the next day. For actually doing the nasty, hotel rooms are out, so it takes place at a casa particular (private house), an apartment rented for $25 or so for the night; often they belong to the jinetera's friends or relatives, who'll vacate at a moment's notice).

Or some foreign guys will already have apartments rented (you can even find them on the Internet, going for $30 to $50 a night). "It's a helluva lot safer than going to some strange neighborhood at night where you have no control of the situation," Dimitri told me.

And there's still a fair amount of sex tourism, even books, web sites, and tour operators devoted to it. Cassirer runs a members organization called TSM Travel, and his book gives horny dudes the lowdown on the best destinations worldwide for hot beaches, hot nightlife -- and hot tail ("Three types of women you'll meet: good girls, bad girls, and good girls you convince to be bad girls!"). The web site has a Cuba update section with weekly reports from more than 100 returning members who describe their adventures in sometimes lurid detail.

"You have a card made up with your casa's address," writes one TSM 'newbie'." "And when meeting a girl, you give her the card and arrange a time to meet at the apartment. There you can get to know each other, have drinks in peace." Another member reports he doesn't like to go to the nightclubs because "you only meet professional women there. I hang out instead near shoe stores. Latin women just go crazy over shoes and that's the best place to meet the nice girls."

Says a third, "I also go to the universities and find the cute girls in jeans and tee shirts. Give her my card, the money for a taxi to meet me there. The problem now is that girls can't be seen walking around with foreigners, so the meeting must be at a secret secure place. Of course in clubs, there's no problem to talk freely, but as I said I prefer the nice, normal girls to the spandex- clad hookers."

The tone especially of the more explicit writing can seem alarmingly predatory, but Cassirer defends his members, pointing out that the women clearly benefit in terms of those coveted dollars, romance, and sometimes even a ticket out of the country. Another guidebook, The New Cuba, by Costa Rica resident Edward Bridges, gives less sleazily presented information on "How to find a nice girl."

One of my own ex-boyfriends, an attractive 27-year-old writer, while in Havana was shocked to find himself shelling out for a hooker for the first time ever. "The girls were irresistibly beautiful, and I thought I'd have a really new experience. Though believe me, I'd never intended to pay for sex in my life." A Spanish-speaking travel companion negotiated the deal for him and even arranged a casa particular in a safe neighborhood. "The prices are 1950's," he said sheepishly. "The very top professional would be $70, but for $35, I had a beautiful, normal girl."

What is it about Cuban women (and men, for that matter) that can drive guys like this do what would've been completely unthinkable before arriving here? "Cubans are very sexy people, and promiscuity has gotten very popular," commented my friend Jorge, who visits here at least once a year. "Traditionally, it was a typically conservative Latin society, but under a system like this, screwing is one of the relatively few inexpensive outlets for fun that young people have." Indeed, when students are sent to harvest sugarcane every December or January, the fields and dorms often turn into a nightly orgy.

And lest you think that all this frolicking is exclusively hetero, there's also a hopping gay subculture in Havana. Saturday night at the exquisite fin-de-siecle Teatro Nacional, I saw the hottest-looking men in town out in force to watch the equally gorgeous dancers in a stunning rendition of the ballet Coppelia. Afterwards, the boys headed up to Vedado's "infogay" in front of the Yara movie theater and (coincidentally) the Coppelia ice cream park, one of the settings for the gay-themed Cuban movie Strawberry and Chocolate. Here they schmooze, cruise, and -- oh my God, is that an actual drag queen?! -- find out where that night's party is being held (there are no gay bars or discos; instead, a small group of professional party organizers take turns hosting these events every weekend).

Bit by bit, the crowd headed off in 1950's gypsy cabs to a house in a far eastern suburb of town, where two friends and I paid $3 cover and find hundreds of fashionably dressed young maricones dancing and drinking in a tree-filled courtyard. Downing a $1 Cristal beer and flirting up a storm, my American friend Jason observed, "You definitely have to watch out for the jineteros on the gay scene, too. But there are a lot of nice, genuine people out there, too, and you can learn how to spot the hustlers after talking with them for a minute or two."

If you've ever watched Cubans dancing, it all happens below the waist -- a real suggestion of what's to come. Here among this well dressed crowd, the hip grinding literally put me in a sexual trance, a frustrating one at that considering that I couldn't have any one of these gorgeous Latin boys. With nonexistent Spanish language skills, I wasn't about to venture out solo to the hetero nightclubs, so I had to content myself by stripping these guys naked, imagining what I might see if the rumor about Cuban men's gigantic size was indeed true. The pants moved to the hypnotic salsa beat as I watched closely.

Maybe I could convert the Ricky Martin look-alike just for one sweet night. I danced along side of him. (Deluded again.) I watched a few gigolos work the crowd. Two left with older Italian men. An irresistibly good-looking guy, dressed conservatively in a cobalt blue dress shirt with cuffs rolled up, targeted my friends Todd and Jason. After he'd lingered around them for a good while and wasn't hooking up, he asked them, "Could you at least give me a few bucks for the taxi home?" What he, like most of the others, was really seeking was an invitation to come for a permanent visit to another country.

So nice and genuine or cold and calculating, how many young Cubans actually make it out? Figures are hard to come by, and the Castro gang sure doesn't make that kind of thing public. But I did watch a lovely young lady getting hitched to a Frenchman in a gorgeous ceremony at the Hotel Nacional. A gay guy named Chino, whom Jason met in 1998, shortly thereafter moved to Milan with his Italian lover. And Milady put me in touch with Caridad, a beautiful blonde 26-year-old who made it to London five years ago.

Cari was born in what before the 1959 revolution would have been a middle-class family in Matanzas, a seaport on the north coast about an hour east of Havana. When she was 12, times turned rough, and got worse when her dad was jailed for smuggling a pig to sell on the black market. After that, she swore that one way or another, she would again live in the style she knew from her childhood.

She found her way onto the world-famous beaches and into the discos of Varadero, the resort area two hours east of Havana (now off limits to most Cubans), and finally snagged an English ad executive who got her a letter of invitation to visit him in London. Bingo! Things ultimately didn't work out for them romantically (surprise, surprise), but she's still there today, working as a waitress and living with a young Italian boyfriend with whom she parties, fights, and lives a normal life. Cari isn't bitter about her past, and still doesn't think of herself as having been anything like a prostitute. "In Cuba you need dollars to live, so everybody has to have a business."

n the last day of my trip, I happened to run into Nikos and Dimitri on a tour of the La Corona cigar factory. They happily reported that Operation Makeup Kit was going swimmingly; I decided I didn't want to hear the blow-by-blow, so to speak. And on the tour itself, in between fending off workers trying to sell us contraband Cohibas, I asked a roomful of stud muffins packing boxes what they thought of the infamous Monica Lewinsky stogie caper. Blank stares. The scandal was all over the press down here, but obviously I guess the more salacious details were left out.

Milady, of course, knew the whole story. "Would you believe it?" she said. "Some Canadian guy wanted to try that with me, and I looked at him and I said, 'Hold on, you want to ruin a $25 Romeo y Julieta just to do that?' Well, a girl has to have some limits, after all."

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