Chapter 5: Dom and Sissy in Wonderland

For the rest of the week during my stay at Bill’s house, he mostly selected the decorated underwear from the box and took great pleasure in flaunting his skimpy attire. Gone were the more manly thongs in exchange for ribbons, bows, and bling. I thought the whole thing quirky but not so much that it changed my view or growing feelings for Bill. I dismissed the voice inside of my head that was asking questions.

On Saturday morning, it was time to return home to pick up Brian. As I packed, I could hear Bill fumbling around in his large, walk-in closet. He called for me to join him. Bill had two large plastic totes on the floor and asked if I was ready to see what was inside. Here we go again, I thought. Feeling I had no choice but to say yes, he nervously opened the lids and took a step back as he motioned me closer to take a look.

One of the totes contained a collection of high-heel, platform stripper shoes in various colors and styles. There was an assortment of fishnet stockings, garter belts, see-through lingerie, and very short-cut-off, daisy-duke shorts. There was makeup and a wig. The other tote contained more adult toys, restraints, and a few things I didn’t recognize or understand how somebody could use them.

I had always considered myself open-minded and I was no shrinking violet, but at that moment, I realized how naïve and cloistered my suburban life had been.

As Bill stood back to watch my reaction, I was doing my best to conceal my disbelief.  I didn’t know what to make of it. I was speechless for a moment as I tried to take it in – all while trying to maintain my composure so as not to send a message that I thought he was some kind of freak. I couldn’t reconcile all of it in my head that quickly.

Even though he liked being submissive during sex and parading around in frilly underwear, he was still very masculine in every way, from his commanding, baritone voice to his muscular shoulders and purposeful stride. It didn’t add up. What did I get myself into?

He finally broke the awkward silence by saying the words, “I’m a crossdresser.” He explained that he liked to wear feminine clothing and to dress up because it turned him on and made him feel sexy. He liked the way he looked and felt. While he was swift to underscore that he was not gay and was not interested in men, that claim was lost on me because all I heard in my head was, “I’m a crossdresser.” 

It was not a term I was familiar with, and I had no experience or point of reference to understand what that really meant. I had only come face-to-face with a transvestite once in my life back in Portland during Rose Festival.  The bad makeup, exaggerated walk, and the tell-all adam’s apple quickly gave him away. My God! Did Bill dress up and walk around town in all this stuff?

I was trying my best to suppress my confusion and hide my face from his view.  All I could think of saying to mask my surprise was, “Where do you find shoes that big?”  I bent down and picked up one of the white sparkly shoes that matched the sequined thong he wore earlier in the week. The shoe was heavy and well worn. He had clothing to match each pair of shoes.

Bill didn’t answer my question about where he bought his wardrobe but instead asked if I was freaked out. I lied and said I was not freaked out at all. I told him it was a bit unusual, but it was his business if he wanted to dress up in stockings and high-heeled shoes. Those were my words, but not altogether my feelings. I was trying hard not to say something that would embarrass him or me. As I turned to exit the closet to return to my packing, I said, “Just don’t let me see you in a dress.”  There was a momentary pause before he replied, “What kind of dress?”  To myself, I answered, “Any kind of dress.”

All I could see in my mind were images of Caitlyn Jenner all dolled up in a gaudy evening gown, and it was playing games with my brain. I wanted to get out of there as quickly as possible but didn’t want to send the wrong message to Bill that I thought he was some kind of aberration. I needed to to think and clear my head.

Bill had pulled back the curtain even further, and I was given a rare opportunity to see what was going on backstage. He showed me the Full Monty.

After I finished packing and was leaving to return home, Bill asked if I was sure I was okay with what he showed me. I assured him that I was and that I would not judge him because he liked to wear feminine clothing. My response was not altogether truthful.

I drove the 45-miles back home with my mind swirling with questions and confusion. Aren’t crossdressers and transvestites the same thing?  Does this mean Bill is a transvestite? How could he not be gay? Weren’t all crossdressers gay by very nature of the desire to be feminized? How could a tough and brawny SWAT cop be a crossdresser?  How did he get away with it all this time? Did his ex-wife know, and did that play a role in his divorce?

It dawned on me that the nail polish wasn’t his ex-girlfriend Sherry’s; after all – they belonged to Bill! I was drowning in images of me pegging Bill with strap-on dildos, the restraints, and his craving to be on the receiving end of oral and anal cock penetration. I realized we hadn’t engaged in traditional intercourse the entire week of my visit. The pieces all came together to form a very different picture of the man I was falling in love with, but the most critical question hadn’t occurred to me yet.  Can I deal with this, and do I even want to?

After Brian was asleep, I fired up my laptop, took a deep breath, and plunged into a whole new world I never knew existed. I got a fast-track education I never thought I would want or need. Typing the word crossdresser in Google produced over 131 million results. The first result that popped up was a definition of Crossdresser under Urban Dictionary, describing a crossdresser as “A person who dresses in clothes typically only associated with the opposite gender. A simple enough definition, but I wasn’t looking for the textbook explanation based on the type of clothing one wears. I wanted to know who these men were and what compelled them to crossdress. Most of all, I wanted to know if this meant Bill was gay but hiding it.

First, transvestites and crossdressers should not be confused with people who are transgender or transsexual as these terms are specific to people who identify with the opposite gender in which they were born. Transgender people and transsexuals basically believe they were born into the wrong body or the wrong sex, and it is about how they feel inside – not what they wear or who they have sex with.

With the increasing attention to LGBTQ causes and gender identity issues, it is not uncommon for people to get the meaning of these labels and their definitions mixed up, and I was no exception. Bill’s revelation allowed me to learn about these communities, the differences between them, and their many struggles to find peace and a place in a society that is uncaring and mostly uneducated about such subjects.

During my research, the information I most embraced was that crossdressers generally do not associate themselves with the LGBTQ community because so many of them claim to be straight heterosexual males who simply like to dress in woman’s clothing. Indeed, there are homosexual crossdressers, but they are allegedly the minority. While some men have motivations to crossdress other than for sexual arousal, many do it for sexual excitement, and that certainly described Bill.

Men who crossdress are not perverts or mentally deranged.  They come from all walks of life and from every socio-economic and demographic spectrum. They could be your boss, pastor, neighbor, favorite football player, or even your husband, and you may never know it.  They are professional athletes, soldiers, cops, businessmen, construction workers, teachers, politicians, and store clerks.  They are everyone and anyone.

The reasons why they engage in crossdressing are as varied as the men who do it. Everything from sexual gratification, relief from stress, being envious of the power of women, expressing hidden personalities to men who report just having an unexplainable need or desire to express their feminine side.

All of the information I read seemed to support Bill’s claim that he was not gay or interested in men per se. Still, he seemed to fall into the category of transvestic fetishism because he became far more aroused and far more easily when he was wearing women’s clothing than when he did not. In fact, Bill really wasn’t all that interested in sex unless he was dressed, sucking a dildo, or being pegged.

It was well after 2:00 a.m. when I finally shut down my computer.  I never imagined I would need to learn so much about such subjects, but I felt empowered with the knowledge I gained and felt better prepared to make decisions as to how to respond. I was convinced there was no reason to stop seeing Bill.  So what if Bill got off wearing women’s clothes so long as he didn’t do it in public and it stayed within the confines of his private life and home. What could possibly be the harm in being involved with a crossdresser? 

According to crossdressers who posted comments, many of them reported being happily married, and in some cases, their wives and significant others embraced and even participated in the activity. The problems stemmed more from the wives who did not know about their husband’s activities and the deep sense of betrayal and shock when they found out. Similar to finding out about an extramarital affair – the devastation happens when you don’t know and find out later.

 I always considered myself to be an open-minded person, especially when it came to individual lifestyle choices. Although I was at peace with the apparent facts of Bill’s sexual fascination, I also knew that allowing someone with this kind of fetish into my life would touch me in a very personal way. Although I felt privileged that Bill trusted me enough to share such an intimate secret, I had not yet been introduced to the demons that drove his behavior.