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Was the outlaw Jesse James a cross-dresser? Probably not, but there is an interesting story of him

dressing as a young lady on at least one occasion.

According to his own son, Jesse Edwards James, the event in question occurred during the summer of 1864,

not long after the bushwhackers struck the town of Plattsburgh.

At the time, Jesse would have still been about a month or two shy of his 17th birthday.

Per Jesse Jr., quote,

Leaving Plattsburgh, the guerrillas crossed the Missouri River to Independence. Four miles from

independence, there was a disorderly house, i.e. a whorehouse, kept by several women, and it was a

resort for the officers of the federal garrison of independence. The guerrillas set up a trap to catch these officers.

Jesse James, dressed as a young girl, rode up on horseback to the house and called its

mistress out, imitating the voice and manner of a girl.

My father told her that he lived not far away, that he was a girl fond of adventure,

and would like to come to the house that night,

bringing two or three neighbor girls to have a good time.

Wink, wink.

I added the wink, wink.

...