Bookies Behaving Badly Part 2: This Cross Dresser Once Feasted on Cocaine

Written by:
Jagajeet Chiba
Published on:

There is a bookie in Costa Rica who was one of the first to settle there at the time this Central American nation was becoming a haven for the world’s sharpest bookmakers.  He had a secret that didn’t stay a secret for very long....nor did he seem to try to conceal it.

He was a bookie behaving badly.

And actually he had more than one secret, the first of which being this bookie (we will call him Bookie X to protect his identity) had a severe drug problem.  His drug of choice was cocaine and it would eventually disrupt his ability to run one of the largest sportsbooks in Costa Rica.  Eventually, Bookie X got the boot, literally we were told. 

A young Tico sportsbook employee once relayed this story to us: “I was at this giant rave party.  Everyone was high on drugs.  The party went on all night into the morning.  The sun was coming up.  It was held at this house and the host, I went to get some coke, there he is standing in this dress with a wig on with coke and other drugs in front of him.  He was snorting coke.  It was…”

It was Bookie X, dressed as a woman.  He hosted this rave party at his own home, or at least that’s what the young sportsbook employee was lead to believe.

But that’s nothing compared to this story that we heard from another sportsbook employee, a transplant from Europe. We will call him Oscar.

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“Christmas 2008 I’m in Costa Rica. With two degenerates, I go to (Bookie X’s) house. we buy 5 bottles of Absolute and 10 packs off smokes.

“He got the rest ‘lined up and ready’,” Oscar continued, making reference to the party drugs provided.  “(The) only problem is we got no food.

“Around 1 am we get really horny and the two guys bring two of six whores that were working the graveyard shift at the Del Rey.”

The Del Rey Hotel is perhaps the single most popular hangout spot for expatriates and locals alike.  Prostitution is legal in Costa Rica.  The women who hang out at the bar – and there are plenty – they are all prostitutes.

“These whores were too f***ing ugly to touch.  (Bookie X) got up and f***ed both.  He was wearing a dress.

“Around 5 am I start to get hungry and see (Bookie X) eating.

“’What the f*** Man!!!!  You holding back food?  A**hole!

“Turns out his nose is so stuffed that he is eating coke. 

“White Christmas 2008,” Oscar laughed.

This, by the way, was long after getting thrown out of that large book he once managed. 

To the best of our knowledge Bookie X has never gone through with a sex change.  He also does have sex with women based on the scene outlined above (then again, some of those Del Rey ho’s might actually be “Joes”).   Studies do indicate that the vast majority of transvestites are not homosexual.

Recent research has confirmed that No one really knows why some men have this desire. “Many men who cross-dress describe it as an outlet for stress, and they tend to want to dress up more during times of tension at work or at home,” notes psychotherapist Christine Webber.  “Some men get relief from tension simply by wearing women's lingerie (often silk) under their exterior male clothing. These guys often go no further than that with their cross-dressing.”

As for the drugs, Bookie X was hardly in the minority.  Bookies residing in the so-called “Switzerland of Central America” easily fell into the party lifestyle.  Many lost their sportsbooks as a result.  Others died.

Today, one can walk into an AA meeting (Alcohol Anonymous) on any given day and see a handful of sportsbook operators taking part.  It’s akin to church. 

Bookie X still resides in Costa Rica.  To the best of our knowledge he is still a cross dresser.  We do not know if he ever sought help for his drug problem.   

Check Out More Bookies Behaving Badly

Bookies Behaving Badly Part 1: Wife Shot 13 Times

- Jagajeet Chiba, Gambling911.com

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