I enjoy city crossdressing because there are great restaurants.

I have always enjoyed city crossdressing because there are so many great restaurants to choose from. People tend to dress up a bit more at the nicer places so I don’t stand out as much. This adventure has me back in Portland Oregon again at the Historic Benson Hotel in the hart of downtown. Built in 1912 the Benson is now in my collection of crossdressing VINTAGE HOTELS and it is definitely one of the more elegant structures.

It is obvious from your first steps inside that you are in a special and elegant place unlike the modern hotels. The rich wooden walls and marble floors are just some of the delights in one of my favorite city crossdressing hotels.

I arrived at the hotel right at 3 o’clock which gave me enough time to get settled and make my 7PM dinner reservation at El Gaucho restaurant. Because I had to skip my August adventure and only dress a couple of days each month it takes me a bit longer to get ready. The layout of the hotel bathrooms is usually different that requires getting used to. Also with such a long gap between outings I usually forget at least one step in my makeup process. If it is crucial one I have to undo something to correct it add time to the process. Fortunately El Gaucho is right next door which I chose for that very reason. I have learned over the years with my city crossdressing to avoid using a cab or UBER the first night to save time. I usually need a little extra time getting ready so walking to the restaurant instead of commuting makes good sense.

CITY CROSSDRESSING DINING

All went well and I walked into El Gaucho at 6:55 and was promptly seated at a table in the bar area.

I enjoyed my meal and my waiter was very professional which is part of what makes the city crossdressing experience. Restaurants in El Gaucho’s classification are typically only found in big cities or very well to do enclaves like Beverly Hills. After dinner one of the managers was kind enough to take the picture of me above and the one across the street in front of the doors.

The doors are the front entrance of the United States National Bank building which was built and opened in 1917. In my city crossdressing adventures I always enjoy it very much when I can visit vintage locations with stunning architecture.