Larry Goodwin says he was wearing a skirt and blouse and shopping for clothes for his wife when he was ordered to leave the Little America Hotel.
He refused and says he was then tackled by security officers and later arrested by city police for allegedly trespassing and disturbing the peace.
Goodwin, 53, is claiming discrimination, and the American Civil Liberties Union is on the case. He's a well-known cross-dresser in his hometown of Douglas, Wyo., who prefers to be called "Sissy."
"I'm outraged, absolutely outraged. Would they treat a man in a three-piece business suit that way?" Goodwin asked Wednesday.
He plans to plead not guilty at a May 25 court date and has filed a complaint with the ACLU, where lawyers say they may take up his cause.
A manager at Little America insists Goodwin crossed a line by acting provocatively and upsetting guests.
"We have many cross dressers coming to our hotel. That wasn't unusual," said manager Klaus Kelterborn, who claims Goodwin kept bending over, "exposing his pink underwear" in the April 17 incident.
Goodwin insists that "the only reason they saw my underwear is because they threw me on the floor and my skirt flew up."