Chapter 7: The Past Is A Preview Of What's To Come

Learning the history of Bill’s crossdressing, how it all started, who else he shared his secrets with, and who participated was not necessarily helpful in my journey from knowledge to understanding. I was naturally curious about how and why a man like Bill with his background got into this kind of intimate entertainment, but his explanations were just dull details, and sometimes the story didn’t add up.

Bill married his first wife, Tracy, when they were in their early 20’s, and both served in law enforcement. Bill claimed it was Tracy who got him interested in wearing female lingerie when she asked him to put on a pair of her panties out of the blue. Bill said he liked the way he looked and how her intimate apparel made him feel – this was one detail I had no trouble believing.

Bill said Tracy first suggested they engage in dom/sub-role-playing, introduced him to pegging, and added that one of her fantasies was to watch him be fucked by a guy from behind while he performed oral sex on her. This fantasy was not surprising coming from Bill until he said he attempted to make it happen. Somehow, Bill found a guy willing to engage in that kind of threesome, and they arranged to meet in a hotel room, but the guy never showed up. I didn’t ask Bill how he found that guy, but I figured it out later.

Bill described Tracy as a very promiscuous woman, which eventually led to their divorce when she came home one day and announced she was pregnant with another man’s child. I had no reason not to believe his explanation of how and when he got started with crossdressing, but while the sad saga about Tracy and their marriage is true, I no longer believe this account of how and when his fetishes began. At best, it is a gross twist of the facts.

I now believe a closer version of the truth is that Tracy was the first woman Bill exposed his interest to, and she, like me, embraced and participated in it because it appeared harmless, and she wanted to please Bill. Tracy had some pretty kinky sexual interests herself that Bill was all too happy to oblige since it served his “private” needs as well.

I suspect Bill was engaged in some form of crossdressing long before he married Tracy based on the stories I heard later. In one account, Bill described an older guy he worked for while in high school that he suspected was grooming him for a sexual encounter. When I asked if this guy ever made explicit advances, Bill said no, but I have my doubts about the complete truthfulness of his answer.

Bill alleges his second wife, Shannon, never knew about his crossdressing even after 15 years of marriage. Unlike Tracy, Shannon was prudish when it came to sex and life in general.  A few years into their marriage, she became fanatically religious and developed a sour attitude toward sex.  He proclaimed Tracy would only have sex in a missionary position because anything else was a sin. Although Bill said she was not at all like that when they first met, she got back into religion after their daughter was born. It eventually became rare for them to engage in any kind of sex after her religious reawakening.  (As much as Bill disliked traditional intercourse, I doubt it was much of a sacrifice.)

To test Shannon, Bill said he once wore a man’s plain, black thong, and Shannon was so disgusted at the sight of it she sent him a text telling him never to let her see him wear it again. Bill said for years when she would go to work and he was alone during the day, he would dress up and masturbate to porn. Bill kept his secret wardrobe locked in his gun safe along with an assortment of his favorite sex toys.

Still, I wondered how he could conceal this erotic obsession from Shannon for nearly 15 years and how someone with his sexual prowess could live under those pious conditions.  Like many married people, he said he stuck it out as long as he did because of their young daughter. I would later learn that the impetus for the split was not only allegations of infidelity but Shannon’s absolute intolerance for Bill’s drinking – something he also tried to hide with far less success than his crossdressing.

Bill also claimed the woman he was dating when we met also did not know about his crossdressing. He tempted her acceptance by wearing one of his purple man-thongs, and when she laughed at him, he never tried again. Still, their relationship lasted over a year, and Bill was still seeing her when he joined the dating service. Text messages I found even after we moved in together also revealed his broader deceptive tendencies.  I didn’t necessarily believe his explanations but accepted them to move on.

In spite of curious episodes from the past, life was good.  We were comfortable and things were going well, but living together under the same roof, day in and day out, also meant that the angels of the present and the devils from the past would eventually meet.