THE BIG, BIG BUILDUP!
In my mind, at least, there are some things to do that are so big, so risky, so classic, that they form Events in the Olympics of Crossdressing! (trumpet fanfare, please)
One of these is going dressed to Tijuana, Mexico.
Tijuana, for those unfamiliar with the place, has QUITE a colorful history. Its first big time was as a place to get a drink during Prohibition. It was also a base for liquor smuggling into the US. So during the twenties, it began to earn an unsavory reputation, as a playground for the wealthy, the famous, and the infamous.
During World War II, a whole generation of sailors and Marines, stationed in San Diego or just passing through, went "down to Teejay" for a raunchy evening's entertainment, with baudy nightclubs ("come look at the girls!"), cabdrivers offering prostitution ("wanna meet my seester?") and perhaps delivering you to some abandoned hovel twenty miles out in the desert(!) as well as illegal and legal gambling and drugs.
Transsexuals know Tijuana as the city where you can easily get prescription drugs such as hormones without a prescription. The slightly bigger challenge, of course, is getting them back into the U.S. To do that, legally you DO need a prescription.
And a few in our community may remember Tijuana as the home of the notorious Dr. Brown, an American surgeon infamous for doing whatever surgeries people wanted, no questions asked, but often doing a sloppy job of them, and in later years, in often unsanitary conditions such as motel rooms or garages. He lost his license in the U.S. and moved to Tijuana. Finally, he got so bad that he lost his license in Mexico too. One of his last cases was a fetishist who wanted him to amputate his leg for kicks! He performed the surgery in a motel room, but the man died from massive bleeding.
In recent years, Tijuana has made the news for Mexican crossdressers who were routinely arrested for prostitution.
And finally, Tijuana and some other border towns have allegedly notoriously corrupt police departments, where bribery is a way of life and people are arrested for non-existant crimes just to obtain bribes.
As I re-read this, I wonder why I went there at all!
Like I say, it's an event in the Olympics of Crossdressing. Think challenge!
THE REALITY (WHICH IS UNDERWHELMING COMPARED TO THE BUILDUP)
My wife and I went there Monday. Had a pleasant, largely uneventful day.
We walked in across the border (good exercise) from San Diego. Walked around downtown. Many of the stores have barkers standing outside, inviting passers-by to come in and see the incredible bargains ("we're almost giving them away, folks!") We looked into custom-made leather skirts, but at $150 USD each, they were just too pricey for our current budgets.
Then it was time for lunch. We ate at Sanborns, which is a branch of a large Mexico City-based chain. Had the same dish I ate in Mexico City some thirty years ago! As I recall, it was a LOT hotter in Mexico City! The food in Tijuana is mild, very much the same level of spiciness as you find in Southern California. It was delicious.
On the way walking out of the city, we discovered that the barkers are not nearly so friendly when you're walking out of the city. Overheard some subtle verbal abuse in Spanish directed at my transgenderedness. They probably didn't realize I speak Spanish fluently
And I was being READ!

Oh, the shock of it all!
So we got off the main street and the abuse stopped.
Got back to San Diego with very tired feet! But all in all, a good time!