Reading Mike: The Annotated Bailey: Chapter 8, page 153

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Bailey Commentary

[153] 8 Terese and Cher

tion, and the art faculty began to buy his paintings. He kept quirky hours, working at all hours of the night at a studio, where he could usually cross-dress in private. He ultimately dropped out of college because he thought he could make it as an artist. Cher refers to what followed as Chuck’s "Bum period." During this time, Chuck began feeling depressed about cross-dressing because it made him feel "freakish" and "lonely." (Chuck was still a virgin, and did not have an active dating life.) He sought behavior modification therapy, and stopped cross-dressing for about five years. During this time, he met and confided in a psychologist, who, Cher believes, wanted to cure Chuck, and they became romantically involved. At age 33, Chuck lost his virginity. Chuck did not find the relationship gratifying, however, and the relationship did not last.  
After the break up, Chuck was driving through a poor neighborhood and noticed a wig in a garbage can. He stopped the car and waited, struggling internally with the intense urge to get out and get the wig. He drove on, but after a few blocks the urge was so intense that he drove back to the garbage can and collected the wig. Oddly, there were a number of other women’s clothes with the wig—Cher suspects that Chuck had stumbled upon the results of a cross-dresser’s recent purge. Soon after this, Chuck made peace with cross-dressing, and stopped worrying whether it was normal or acceptable.

This began a period in Chuck’s life marked by a devotion to cross-dressing that was both obsessive and highly creative. He began collecting pornography that featured pictorial stories of women in various stages of dress and undress (nurses, stewardesses, and so on). He would search junk clothing stores and clothing catalogues to recreate their costumes, and would cross-dress and fantasize about them in private.



Chuck’s fantasies began to involve more than looking like a woman. Increasingly, he began to fantasize about having a vagina, and about being penetrated by a man. He was not attracted to any specific man, and he did not fantasize about specific men, only faceless men, and their penises. He enjoyed the fantasy of being physically dominated, as well as vaginally penetrated, by a man.

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