I am a cautious traveler in many respects and my Portland crossdressing Christmas adventure is no exception. Because the Rose City “T” Girl Christmas party is so close to the Xmas holiday I decided to arrive a day early to minimize possible travel delays. The original plan was to meet Sherri for dinner but she came down with a bug and had to cancel which meant I was on my own. OMG here I am in a strange town all by myself dressed to the nines what will I do? No problem! I just went to the restaurant and informed them that Sherri could not make it and it was just going to be me.


The restaurant, Ringside Steakhouse is great I was there before last February and enjoyed it. The young hostess took the change in stride and because I was a bit early asked me to wait a couple of minutes while they got my table ready. I was worried they would stick the transvestite in the corner facing a broom or somewhere else out of sight. That was not the case when a lovely young woman escorted me to nice booth in a great location. When she complimented me on my jacket I knew we were off to a great start.


Miguel my server came over promptly and introduced introduced himself and welcomed me back which was a bit strange as I don’t recall meeting him. Maybe he is a subscriber to this blog and read all about my February adventure. Miguel was very professional making sure everything was to my liking especially when he came back to see if my Cosmo was done correctly. He was just as thorough with every other aspect of my meal checking the temperature of my steak and other extra details. He even checked to see if there were empty seats at the bar so I could have a nightcap.

Unfortunately the nicer restaurants in Portland shut down before 10 pm so you have to move to a cocktail lounge to drink later. Venturing into a strange bar in an unfamiliar location is not a good idea so I decided to have some photo fun back at my hotel.





Very nice pictures and story. Hope you continued to have a nice time… Staci
Micki I love to read posts like this one. It’s gratifying to read stories from seasoned veterans of the game that sound quite similar to stories from rookies like myself. (I know I’ve stayed at that hotel before, years ago, in drab of course.) Your dinner companion cancels and you said ‘screw it,’ I’m all dolled up so I’m going anyway and had a nice experience. I find it an interesting dichotomy that “girls like us” are nowadays the best dressed bunch in busy restaurants. I personally appreciate a style of dressing that would be “old school” today, elegant clothes, nylons of some type a must. If it’s real women wearing them or pretty trannies, so be it. I’m just happy somebody is. My wife’s attitude is “we ladies served that sentence while we were working.” Well as a retiree now, I’m glad I’m able to do my time in those type of get-ups. You always look stylish and “the whole nine yards” when I see you here and just wanted to let you know I think it’s great.
Grace Palmer
Thank you Grace for all your kind compliments and encouragement.