June 15th, 1989. Geraldo Rivera’s talk show brings us this segment with Kary/Bob and his partner Laura.
“…he told me that he liked wearing women’s clothes. Well that was probably the biggest shock…knowing for sure that was what he wanted to do…”
We hear from Laura about their relationship, and how she didn’t know her man’s fantasies at first. She describes he didn’t hop into bed with a nightgown on day one, it was an ongoing process. Bob goes on to describe how he is able to express himself with female attire, whereas some of his personality traits aren’t acceptable to society as a male. He claims the longer he’s in the clothes the more feminine his personality becomes.
Cross-dressing and beyond exist well into 2026.
This day, Geraldo’s television history.