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The story makes more sense if you read the chapters in sequential order.

[mylifewithacrossdresser]

The story makes more sense if you read the chapters in sequential order.

[mylifewithacrossdresser]

Chapter 15: Comfortably Numb

One of my favorite songs is Comfortably Numb by Pink Floyd from their epic album, “The Wall.” To me, the lyrics

I can’t explain, you would not understand This is not how I am I have become comfortably numb

underscore the desperate mindfulness of the deep sadness that occurs when we experience loss. A loss that carves out our pain but the human spirit and a need to endure.

My followers sometimes ask me why I don’t just leave Bill after all he has put me through when I have the financial and physical means to do so. I have often thought about it, but my answer is always the same, and it is not a poetic response to simply say, I have become comfortably numb – rather, it is the veracity of my state of mind.

My happiness is not my priority, and I have become numb to the grief he has caused me. My son’s security, safety, and happiness take precedence for now, and creating an upheaval from another divorce could jeopardize the stability he needs at this stage of his life. Perhaps when he graduates from high school in a few years, I can refocus on what I want and need out of life. I think about it – even dream about what it would be like to have peace of mind once again.

I may not have to wait that long as it is also possible that Bill may come to the same conclusion that he needs to pursue a life that will make him genuinely happy and one where he can be his true self – whatever that is.

Stay tuned.  The story hasn’t ended yet.

[mylifewithacrossdresser]

Chapter 14: Betrayal Burns Hot

In life, things don’t happen to you – they happen because of you.

Scorpions take refuge from the cooler fall weather by finding their way inside the house. Bill takes care of them. Spiders, too. Our air conditioning filters need to be changed every few months. Bill takes care of it. The bathroom faucet started leaking last week. Bill fixed it. I had to go to the emergency room a while back and was admitted for surgery. Bill drove me and sat with me in the ER until I insisted that he return home.

We have a beautiful home, live well, and look forward to a comfortable retirement. We have traveled to Hawaii, Tahiti, Mexico, Key West, DC, and took a magnificent train trip across the Canadian Rockies. We make great travel companions, and I can always rely on Bill to take care of things.

Still, Bill has his secret vices and lives with demons I can’t even begin to know. There is very little affection between us these days, and sex is mostly a distant memory. I would have been justified in leaving him countless times over the past six years, and I came very close on several occasions. I found an apartment close to Brian’s school and was literally writing a check for the deposit when I received a text message from Bill that said, “I don’t want to lose you.”  Reluctantly, I left the rental office and went home. This scenario repeated itself several times over the years, whether it was me looking to escape or whether it was Bill. Somehow, we always pulled through, but the erosion of trust is permanent. It never will recover and I have had to come to terms with that condition.

I thought about having an affair of my own as a form of retaliation and self-validation.  Of course, I thought better of the idea. There was no sense in making the situation even worse or lowering myself to Bill’s standard of fidelity and integrity. Bill has the addiction, not me.

I suspect it was the onset of COVID that ultimately put a damper on Bill’s extracurricular sexual activities. At first, he was convinced COVID was not real, a media-created sensation to bring down Trump’s administration.  Just another form of the flu for sure, he insisted. That baseless attitude changed when Bill learned of active and retired cops he knew and respected who succumbed to the disease and were dying in record numbers.

As for Bill’s crossdressing, I have grown a complete disdain for it. What used to be innocent, fun, and quirky became a daily reminder of what Bill was up to behind my back because his dressing was part and parcel of his debaucheries involving other men. At times I felt as if he was competing with me for who was the most feminine and compelled me into a role I never wanted. I try not to look at him getting dressed as he selects his silly-looking panties, pulls them on, and admires himself in the mirror. When we get pedicures, Bill usually wants me to approve of the shade of pink nail color he selects, but I just shrug my shoulders and say, “Whatever you like works for me.”

Bill is free to do what he likes and to engage in whatever makes him happy, but these days, I shy away from giving his obsessions any kind of validation. I do my best to ignore it all, which is torture for someone like Bill who relishes in the exhibition.

My experience with this underground world started with a hint of knowledge and the journey has ended with a fuller understanding of what drives this behavior. Knowledge about something is not the same thing as understanding it. I genuinely suspect Bill is gay, but not in the sense that he wants a romantic relationship where he would walk hand-in-hand with his partner at gay pride parades. His attraction to men appears to be purely sexual, but then one can never be sure.

I believe, too, that Bill’s marriages were mostly a disguise or a front for his true self. An identity that he could not possibly undertake as a way of life. Certainly not in the male-dominated and masculine profession of law enforcement, being on SWAT, and serving as a high-ranking officer. While he took astonishing risks in his sexual endeavors, he could not possibly risk people knowing he loved dressing in feminine lingerie or engaged in homosexual encounters with trannies.

On the positive side, Bill’s neat, likes things organized, is financially responsible, likes to travel, is willing to watch classic movies, and loves Sunday football – just like me. Accepting our life together as agnostic roommates has been beyond difficult. The betrayal still burns hot and I grieve the loss of a husband I never really had.

[mylifewithacrossdresser]

Chapter 13: Everything Is Different But Nothing Has Changed

Many of us live in the space between what is and what might have been.

Our disastrous trip to Palm Springs was a turning point in our relationship – at least for me. I never felt the same way about Bill again. During the four-hour trip back home, I thought long and hard about the night before and the three years since we met online. Somewhere along that ugly and parched stretch of the I-10, I realized how oblivious Bill was to the pain he inflicted. Earlier that morning, he had gone about his morning routine as if nothing had happened.

I finally understood just how impenetrable he was – like a slab of granite – nothing got through – not emotion, not warmth, not regret, not sorrow, not affection, and certainly not guilt. Like granite repels water and heat, Bill repelled almost every human emotion known – except when it came to certain sexual desires. Only then does a kind of peculiar passion emerge.

I wasn’t serious about suggesting an open marriage. It was more of a test that I knew Bill would quickly dismiss. However, in my mind, Bill was already benefiting from a one-sided open marriage that he decided and defined for himself. Bill did not view his sexual encounters or internet pursuits with other men as infidelity and denied violating any marital principle where there was an assumption of exclusivity. Bill described his involvement as a kind of “voyeurism” which I found ludicrous. These specialty websites were not a place you go to “flirt” – rather to find like-minded people who are willing to take great risks to fulfill a deep-seeded need.

As I thought about all these things, I suddenly realized something was different and missing. My emotional response was somehow changed. I searched for the powerful and debilitating emotions I had experienced only a few hours earlier, and they just weren’t there. I had cried all of the feelings – and the love – right out of me.

It felt as if I had been suffering from a long-running fever that finally broke. I felt remarkably better. I was calmer, cooler, and even relieved. I was determined to pursue happiness on my terms. To find contentment and enjoyment again – with or without him. The release felt so wonderful I almost burst out laughing.

The transformation wasn’t as immediate as it sounds.  For days, weeks, and even months after, there were still incidents that reminded me that everything was different, but nothing had changed. The difference was, I was no longer spending countless hours in a game of hide-and-seek, searching for evidence of wrongdoing, or agonizing over the injury. I came to accept that no matter the risk, the consequences, or the pain Bill inflicted on me or our relationship, come hell or high water, he was never going to give it up. It is the very definition of someone who is afflicted with addiction.

Over time, the bleed of my feelings was nearly complete. The final separation occurred after the accidental discovery of a hideous mask Bill had added to his special wardrobe. This was no cheap Halloween mask. The mask was that of a female, complete with eyelashes, bad makeup, and long brunette hair. The opening for the lipstick-covered mouth was unusually large and for good reason.

Although I was no longer searching his computer or phone for clandestine pursuits, sometimes things would happen right before me when I least expected it – like pulling up to a busy intersection just in time to witness a horrific crash. Driving through a few seconds earlier, and you would miss it – a few seconds later, and you would miss it. But sometimes, you’re at the precise moment when it happens, and you have no choice but to watch.

It was quite by accident that I came across the mask when I was looking for a pair of sunglasses I had left in the truck. I knew right away Bill wasn’t driving around with that mask in his truck because he was robbing gas stations on the way home from work. I had a pretty good idea what he was up to, and it was nauseating and grotesque. I realized that just because I was no longer hunting for evidence of what he was up to didn’t mean he had stopped. Of course, Bill offered the same old excuses, denials, and lies, but none of it angered or caused me the same kind of intense pain the way it once had.

Soon after discovering the mask, I began to lose interest in other aspects of our relationship, mostly sex. (I won’t say I missed the intimacy because that implies closeness and tenderness, which rarely existed.)  I grew tired of the pageantry, the CD outfits, the toys, the poppers, and dildos that were never big enough. I detested the theatrics of it all. I felt as though I was nothing more than a prop, a stand-in, and a poor substitute until Bill could arrange for the real thing. I didn’t intend to lose interest – it was just the result of the unintended consequences of cause and effect.

Eventually, the anger, frustration, resentment, and heartache I experienced for those two-plus years were slowly replaced with indifference and apathy. Today, I no longer agonize over the defeat, questions about whether I made a mistake nor am I paralyzed by grief or self-doubt. Those are distant feelings I left behind in Palm Springs in a torrent of tears.

[mylifewithacrossdresser]

Chapter 12: Palm Springs - Oasis For A Different King

As we approached our 3rd anniversary in early March 2018, I had spent over two years of our marriage trying to uncover Bill’s secret and compulsive sexual endeavors. Nothing was illegal about it, and there wasn’t anything necessarily wrong with his obsessions except the fact that he was married, cheating, and engaged in dangerous conduct that put him and me at significant risk. Every discovery and confrontation included a question about his sexuality, but Bill continued to reject any suggestion that he might be gay.

At times, I resorted to extreme and expensive means to uncover and follow his activities. Besides hacking into his computer and phone, I sought the help of a sex therapist to help me understand the psychology behind this behavior. She also helped me to offload some of the emotional burdens that this situation caused and to understand sex addiction. It is much like all other addictions. The person afflicted with it is willing to risk anything and everything to experience the rush of the next “hit.” The reward and thrill of it all are worth the gamble, and so are the consequences – no matter who or what is sacrificed.

The services of a private detective tracked Bill’s whereabouts when I was forced to travel for work. He also turned me on to software used to track web activity and record all keystrokes while using the web. The use of this software exposed the grotesque genre of porn Bill was obsessed with involving a form of hypnosis and the use of poppers to desensitize the viewer to women’s sexual anatomy and the desire to have sex with a woman. It was a kind of feminization using”cock worship” scenarios where trannies instruct the watcher into controlled responses upon command. Bill spent every moment he could watching these videos to complete his “feminization.”

It became more difficult to track Bill’s activity when technology advanced as privacy advocates shaped the future of web activity with mobile apps. You can download an app to your phone where you are issued a legitimate private number for a fee. Text messages and phone calls do not appear on your mobile provider’s account because the phone activity is not routed through their servers. Apps such as MySudo even offer a private email domain.

Bill moved from using his computer to CoverMe, an app offered through Apple. This service not only issues a private phone number but features a private vault where photos taken with your camera are stored in the “vault” so they cannot be viewed in the camera’s photo book. CoverMe can also be camouflaged behind an icon that appears as a news app on the screen. (So clever.) Messages are encrypted and the app is easily closed by gently shaking the phone. I learned that Bill had downloaded both MySudo and CoverMe to his phone when the Apple receipt for the purchases appeared in his email account. I confronted Bill about purchasing these apps a few days before we were scheduled to go to Palm Springs to celebrate our anniversary. As always, these confrontations resulted in more denials and a huge argument that went nowhere.

I was going to Palm Springs with or without him. I remember liking the area’s terrain, and I was looking forward to a change of scenery. Most of my impressions of Palm Springs had been formed from the 1950’s stories of old Hollywood glamour with Frank Sinatra and Bob Hope. I would soon find out that Palm Springs had become the largest gay community in the country.

Bill decided to go on the trip only the night before our departure when he saw me packing. This time, I refused to pack his special clothing as I usually did when we traveled. (Our travels had become some kind of stage for the BDSM games as if that were the sole reason for the trip.)  The drive took over four hours, and we hardly spoke a word the entire way. The only break in the silence occurred when we took the aerial tramway to Mt. San Jacinto State Park and took in the breathtaking views of the Coachella Valley. A drink at the Lookout Lounge also helped thaw things out before we headed to the resort.

Tired from the drive, we dined at the hotel restaurant and headed down to the hot tub after dinner. It was a large spa that easily seated 10 people without feeling crowded.  Bill was wearing traditional men’s swim shorts, but the 3-inch sparkly jewelry dangling from his belly button was hard to miss. There were two other occupants – both men in their late 30’s. I didn’t think much of it until two more men showed up and then another two.  Before long, I was the only woman in a spa of seven men, and it became clear that they were all gay. Suddenly, I felt extremely out of place. I wondered what Bill was thinking – he had to know but showed no awareness or concern for my growing awkwardness.

Later that evening, while Bill slept, I flipped through the area magazines and tourist books where I learned just how gay-friendly Palm Springs was, including gay-only resorts that catered to people looking for acceptance and privacy. Somehow, I had missed identifying resorts that catered to the gay community when I searched for places to stay. As it turns out, our hotel was located in the heart of where most of the gay bars and nightclubs were located off E. Arenas Road. I looked over at Bill. The covers were off, and he was wearing a pink mini G-string. I remember thinking, “My God, what have I done?”   I had taken an alcoholic to the liquor store.

The following day, I noticed Bill had put on a pink rhinestone stud in his ear before we headed out for brunch.  Within a block of our hotel, it was apparent we were in the heart of the LGBTQ community, with bars, clubs, shops, and restaurants adorned with rainbow flags. Transgenders easily outnumbered the straight, but I noticed several elderly tourists walking down the sidewalk who seemed perplexed and pointing at young men dressed in over-the-top makeup, wild outfits, and high heels.

I popped in and out of boutiques and galleries, but Bill mostly waited on the sidewalk where he never stopped looking at and typing into his phone. We were still avoiding conversation, and I was beyond irritated at my suspicion of him communicating with his special friends through his hidden app. It never stopped.

After two Bloody Mary’s at lunch surrounded by gap couples, I began to openly taunt Bill about his earring, the hot tub company, and how he brought the perfect wardrobe for the local flavor of the community. “Why not wear some of it next time we were out and about?”, I asked. “You would fit right in.” He was not amused – and neither was I. The game of hide and seek was over.

The argument that ensued once back at the hotel was more than just laying out a laundry list of the details of his secret activities involving like-minded men. Suddenly, I reached a peak of emotional distress that resulted in uncontrollable bouts of hysterical sobbing and a state of delirium. Two years of the mental anguish of trying to cope with Bill’s compulsive behavior, the lies, the secrets, the denials, the blow to my sense of self-worth had become too overwhelming to deal with in a setting where CDs and transgenders surrounded me.

My emotional breakdown went on for hours late into the night. Bill was so furious with my uncontrolled weeping and having to witness the consequences of his disloyal conduct that he resorted to looking for another hotel. Sarcastically, I suggested one of the many gay resorts, which only enraged Bill even more. I didn’t care. I wanted to hurt and humiliate him as he did to me.

It was well after 2 a.m. when the crying finally stopped. Bill had stood in the same spot for hours, leaning up against the wall staring at the floor. During the entire episode, he said very little. Bill offered no apology and didn’t even try his usual denials or his accusations that I was delusional. I never learned why he didn’t leave for another hotel. I didn’t care. I sat on the end of the bed, staring out the glass door in a kind of catatonic state, totally exhausted. The last thing I remember was laying back on the bed mesmerized by the light from the pool below dancing across the ceiling.

When I woke the next morning, my eyes were swollen shut from hours of sobbing. I soaked a washcloth in the cold water from the ice bucket and placed it over my puffy face. I felt better after a hot shower and a double dose of pain reliever for my splitting headache brought on from crying and too much wine.

When Bill was in the bathroom getting ready for the long trip home, I stood in the doorway and stared at him in his pink lace panties. He was going about his usual routine as if nothing had happened. Out of nowhere, I asked him, “Do you want an open marriage?  One where we can each seek out our needs but without repercussions? An agreement that may level the playing field?”  Bill whipped around and shouted, “Of course not! I don’t want any part of that.”

That was the end of the discussion about an open marriage that I brought up just to rile him. However, it wasn’t the end of the changes that were in store for both of us.

[mylifewithacrossdresser]

Chapter 11: The Truth Has It’s Own Gravity

Trust is a fragile and delicate thing. From the moment we’re born, our life is placed in the hands of others we want and need to trust, from those we choose to be in our lives to those we do not choose, such as a parent. Traditional wedding vows include words to love, honor, cherish, respect – even obey, but there is no mention of trust or honesty.

The illusion of trust was shattered when I discovered Bill using Craigslist to hook up with other CDs.  On the surface, everything seemed relatively normal in the weeks and months that followed. We carried on our day-to-day routines, celebrated our first wedding anniversary, traveled, worked on remodeling the house, and continued to play our dom/sub games in the bedroom as if nothing had happened.

It was a weak façade as there was a deep and swift undercurrent where suspicions stayed, where unanswered questions waited, and where secrets continued to thrive. The voice in my head was constantly telling me to pay attention because something was off. Subtle changes occurred in the aftermath.

Bill quickly changed his computer password, but I had full access to his email through our internet provider, and he knew it. His email and phone were clean – no unusual texts, contacts, photos – nothing.  That in itself was suspicious.

Bill was suddenly adding to his femme wardrobe with the most raunchy and slutty attire he could find – mostly from online vendors that specialized in this kind of clothing. He was never into wearing women’s “street” clothes, such as dresses, gowns, skirts, blouses, etc. Bill was into the skanky whore look, such as ripping holes into his stockings to give him a trampy feel. Bill was also asking me to take more and more photos and videos of him dressed in trampy outfits, in lewd poses, and close-ups of his back-end stuffed with dildos and nasty words and phrases written on his butt.

In early July of 2016, seven months after discovering the reply to the Craigslist ad, I found a portable flash drive Bill kept hidden in the lunch bag he took to work each day. I copied it to my computer and pulled it up the next day after he left for work. One password-protected document was labeled “Accounts,” but I hacked it open on the third try using one of Bill’s favorite passwords.” It contained a detailed listing of user names and passwords to all of Bill’s accounts and website services. One category was titled “entertainment” and held the login information for the various swinger sites we had been on the year before, but one website I was not familiar with from our pursuits – “Fetlife.[1]”

Naturally, I pulled up the website and entered his user name and password to access the account. The screen came to life with sexually graphic images of Bill from the photos I had taken of him during our erotic role-playing. Although Bill’s face did not appear in any of the pictures, every other part of his body was exposed.

My jaw dropped, and I gasped for air as I scrolled through dozens of his profile photos and explicit comments from his over 50 ‘friends and followers,’ most of whom were men who commented on his ‘sweet ass’ and how much they wanted to ‘take it’ long and hard. Bill wrote in his profile summary that he was a ‘sub’ who loved cocks and the taste of cum and how he wanted to experience being bottomed. He described in exact detail wanting to sit on top while being penetrated by a guy on the bottom. In the gay community, one is either a self-proclaimed top, bottom, or versatile, meaning they will give or receive oral and anal sex. Bill had no interest other than being on the receiving end of whatever his friends were willing to give.

Bill communicated regularly with one follower who repeatedly invited him to attend gay sex parties in the local area. The most recent exchange with his special fan was only a few days prior when Bill was invited to participate in a gay orgy in a hotel room that evening.  Bill replied, “LOL.  Can’t make it tonight, but maybe next week.” (That next week, I was scheduled to travel on business and would be out of town for three nights. I never made it to the plane.)

My hands were shaking so badly I could hardly control the mouse. I managed to click on the link to Bill’s account and discovered he launched his profile almost immediately after we clashed over Craigslist in early December 2015.

As I read through his profile and the countless posts, my body finally gave way to the distress, and I started to hyperventilate. I pushed myself away from the desk and wandered aimlessly through the house, uttering “Oh My God” over and over. I made my way to the kitchen just in time to vomit in the sink. The shock had drained every ounce of energy from my body. No longer able to hold myself up from emotional exhaustion, I fell to the floor in a heap sobbing uncontrollably.

I had no idea how long I laid on the floor; I must have passed out. The familiar sound of my cell phone ding, signaling an incoming text, awakened me from the catatonic state I had fallen into after the tears stopped. It was Bill asking me how my day was going.  His casual banter made me sick all over again, but this time rage replaced tears.

Ignoring his text, I forced my way back to the computer. Glowing from the oversized monitor was a photo of Bill stretched out face down on the bed, his ass stuffed with a big black dildo and the words ‘cock slut’ written across his butt in purple ink. I sat down again and checked out the rest of his profile, where I quickly learned the mystery of the characters ‘jtomv.301’ associated with the Fetlife entry in the document.  It was a Gmail address. He had left off the .com, so I didn’t recognize it as an email. Until then, I also hadn’t realized the characters were his PD call sign and badge number.

Could he have been that obvious and stupid? I pulled up Gmail and entered his email address along with the same password he used for FetLife. It was all too easy to access. I typed the letter “C” in the To field of the address header and saw all of the Craigslist addresses to the personal ads he had responded to since creating his secret email.

I typed each letter of the alphabet in the address header and identified dozens of other contacts after they escalated their online relationship beyond Craigslist. At this point, I was so disgusted and angry I forgot to print screenshots of his profile.  It was a mistake I would come to regret, but a mistake I would not make again.

It was a sobering thought to think about the health risks I might have been exposed to through his exploits with other men. I was incensed that Bill had jeopardized me in such a manner and for such selfish reasons. The visceral hatred I felt for Bill at that moment was overwhelming. The only thing I was thankful for was the fact that Brian was with his dad because the confrontation that evening and the fallout in the days that followed were brutal.

The discovery of Bill’s profile on Fetlife was just another episode in a long string of discoveries of him pimping himself out to other men over the internet that would continue for several years afterward. Bill had no idea I had uncovered his Gmail account or was accessing it to uncover his activities and private communications with his CD friends. A few weeks later, I watched in real-time as Bill took photos of his erect dick bulging from a pink thong and emailed them one of his Craigslist friends. He was in his truck just down the block from our house.

It took longer to figure out his computer password, but eventually, I figured it out. His internet browsing history revealed an addiction to gay porn, but a very particular kind of gay porn that involved passable trannies and inhaling poppers as part of a disturbing form of hypnosis aimed to feminize the viewer and turn them off to wanting real women. It was a form of feminization.

For the next two years, Bill and I engaged in a macabre game of hide-and-seek.  Bill would hide his exploits, I would find them, expose him, and the cycle of denials and promises to never do it again would start all over. The one question I always asked was why he married me? And, I always made the statement that he had no right to live two lives. If he wanted to live the life of a single man to do as he pleases and with whom, he was free to pursue that life, but he could not continue to be married – not to me.

The sex therapist I engaged to help me understand the psychology behind his behavior was convinced Bill had a kind of sex addiction that she thought he used to ease his suffering from PTSD during his time as a cop. She had treated many clients who had various types of sex addiction, but she said she had never encountered a case such as the one I presented. Bill attended one session and was so hostile, he refused to even tell her his name.

Bill was never sorry for anything except getting caught. He was sorry I felt the way I did and that I chose to believe “certain things about him,” but he was never sorry or apologized for hurting me.  None of it was what I believed, but rather what I knew. It was also beyond maddening to experience him try to escape blame by transferring the anger back at me as if I were doing these things to him.

The time I spent seeking the truth about Bill’s secret behavior and his sexual addictions was emotionally and physically exhausting – it made me ill, but the truth has its own gravity and one is drawn to it.

[1] Fetlife is a social networking website that began in 2008 aimed at people interested in fetishism, BDSM, kink, and fringe sexual experiences. It promotes itself as a social network rather than a dating site. It temporarily shut down the ability to create new groups in January 2017 when it attempted to eliminate groups that promoted rape and incest. Today, it has millions of members around the world.

[mylifewithacrossdresser]

Chapter 10: The High Cost of Indulgence

After countless conversations about the rules and the risks associated with engaging another person into our sex life, Bill violated the number one rule of engagement when he was caught sexting pictures of himself to an unknown person. That discovery forced me to face the issue of privacy and trust. Is one entitled to privacy when their behavior leads to questions of infidelity? A mere nine months into our marriage, I already doubted Bill’s commitment and truthfulness. Bill continued to duck, dodge, and deny any accountability for what I caught him doing by the pool.

The thought of snooping in Bill’s phone, emails, and private files was an ugly prospect. I had the passwords and the access so it wasn’t a matter of could I but rather should I. When I noticed a substantial increase in Bill’s texting and hiding his phone, the question of should I pry was answered. The voice in my head that I had silenced all those months was now a constant companion providing advice and forcing me to recognize the oddities of Bill’s behavior when I conveniently chose to look the other way.

The mystery of what Bill had been up to and with whom was answered within seconds of pulling up his email. Bill had been on Craigslist for weeks, answering ads from crossdressers and trannies looking to hook up. Most of the ads said discretion was an absolute must as most of them were married and keeping their underground life a deep, dark secret from their wife or significant other – just like Bill.

When you post or answer ads on Craigslist, the communications stay on their servers, which guarantees the anonymity of the name and email address you use to register. Many people, however, move off Craigslist by sharing their email and phone number so you can communicate more freely and easily without having to sign in to the Craigslist site. There is a risk in sharing your personal information, especially for someone like Bill, whose email address contained his real first and last name. Beyond foolish.

Bill was regularly communicating with a guy who posted an ad titled, “CD Looking For CD Lover.” His ad included a photo of him from the waist down, showing an erect cock, legs covered in black silk stockings, and spiked heels. In the lengthy exchange between them, Bill had also sent photos – photos I had taken of him during our sexual pursuits with him dressed in his favorite outfits and crude poses. He was pimping himself out as a “panty boy.”

They talked about how neither one could “host” a get-together and when they were available to meet up. Only during the workweek, they both said, and afternoons were best. They chatted about discretion and how they were keeping their secret desires to stroke and suck real cock and lay together with silk-covered legs intertwined from their wives. Best I could tell, a date, time, and place had not been decided, but this was only their emails. I had no idea what exchanges were occurring over text.  As far as I knew, they had already hooked up and perhaps multiple times.

I learned, too, that hooking up with other CDs was not a recent development or pursuit for Bill. He had left an internet footprint a mile wide that dated back years. I finally understood that the familiarity Bill had shown for Craigslist personals and writing an ad that would produce the desired result was from an experienced user.

The lies and the audacity of his betrayal were surreal. I was beyond seething. The voice in my head was repeating, “I knew it.  I knew it.” All this time, I had provided a comfortable and safe environment for Bill to express himself through his dressing. I encouraged him and withheld judgment no matter how over the top he got with his increasingly slutty wardrobe. He was denied nothing in bed, and I sacrificed my personal sexual desires and need for affection to pander to his particular flavor of erotic cravings. The only thing that was missing was the “real thing.”

The worst thing you can do in this situation is to engage in a confrontation over the phone or text. You lose the element of surprise and the eye-to-eye contact needed to discern more lies or cover-ups. Despite knowing better, that is precisely what I did.  I called him at his office, exposing everything I had discovered, which was mistake #2. This was only the second time in nearly 18 months since we met that I had raised my voice to him – the first being the week before when I viewed his sexting.

When he returned home later that afternoon, the argument escalated when I waved a printout of the email exchange with his “CD Lover.” Bill claimed he was engaging this guy to be a partner “for us,” but that was a lame defense when I pointed out the discussion about discretion and the secrets they kept from their wives. The gig was up, and he stormed out of the house when he realized he could no longer duck from the proof and deny his conduct.

Of course, like so many of us do when we want to get past some immediate and burning pain quickly, I fell for the promises to stop and his insistence that he “didn’t need it,” as I was convinced he did.

The voice in my head had doubts about Bill’s sincerity, constantly pointed out more suspicious behaviors, and reminded me that I would pay a high cost for the indulgence I afforded him.

[mylifewithacrossdresser]

Chapter 9: Seeds of Suspicion

The course of one’s life can suddenly change by the simplest of things.

It’s not uncommon for people to fantasize about a threesome or what it would be like to watch their spouse or significant other having sex with another person, regardless of the combination or ratio of genders. It takes a tremendous amount of maturity, communication, and most of all, trust to engage in that kind of sexual activity. Many people regret it when they come to realize the act itself was not as riveting as the fantasy.  Unfortunately, jealousy, resentment, anger, and distrust are frequent and sad endings.

When Bill posted the ad on Craigslist, I was not at all confident he would find another crossdresser willing to engage in what he proposed.  I was wrong – so wrong. Dozens of CDs responded, but only three met Bill’s careful (and experienced) scrutiny with a photo exchange eliminating two of the three. That left the reply from Steve.

Steve was not a crossdresser but was open to it and most everything else Bill proposed. He even agreed to the condition that there would be absolutely no sexual contact with me and acknowledged the pursuits would be exclusively between him and Bill. Other conditions included no kissing or anal penetration except with dildos or other toys. My role was to pay the Dominatrix, which wasn’t altogether what I wanted from this rare experience, but once again, it was all about Bill.

A few weeks later, after we had drinks to get to know one another, we met at a hotel for the big show. Bill dressed in hot pink platform shoes, white stockings, a pink tutu skirt with a pink see-through thong underneath, and a white and pink polka dot mid-drift shirt. I wore my Dom outfit with black spiked heels, a leather skirt, matching bra, and black lace-up gloves. Steve changed into a plain thong, black stockings, and heels.

The festivities started with a couple of shots of liquid courage. It helped take the edge off the unspoken awkwardness we all felt. Bill and Steve sat side-by-side on the bed, and I was standing in front of them, unsure if it was up to me to say, “Ready, set, go” or what.

Although Bill had told me on several occasions that he had never been with another man, he displayed no anxiety and seemed quite at ease even before the tequila. Bill made the first move when he reached over and began stroking Steve’s cock. Steve returned the gesture, and the game was on.

Bill arranged a second round a few weeks later that played out much as the first but with more intensity. Somehow, the intimacy of their contact appeared so familiar to Bill – he showed no hesitation or nervousness whatsoever. I might as well have not been in the room.  Neither one of them needed me to act as dom this time. All I did was stand around, observe, and take pictures.  

Bill was quick to try for a third, but Steve came back with a few conditions of his own. One was that I was directly involved and on the bed with them.  Two, there was less oral sex between him and Bill. Having me involved in that way was not an option for Bill, and that was the end of our dates with Steve. Bill went back to Craigslist with a new ad, but nothing panned out – or so I thought.

Six weeks later, I returned home from dropping Brian off at his dad’s house and running errands. Through the kitchen window, I saw Bill sunbathing naked by the pool; his tan skin glistened in the sun. I remember thinking how handsome and sexy he was – and how much I missed the intimacy of making love – the crummy ol’ kind Bill disliked.

Margaritas sounded good along with surprising Bill by walking out with no clothes on, but before I could turn around, Bill picked up his phone and began typing. Because of the angle of the sun in early December, Bill had moved the lounge chair close to the house, and it was clear he was receiving and sending texts.  I didn’t think much of it until he unexpectedly began stroking himself to an erection. Moments later, he began taking a video and snapped several pictures of his achievement.

My initial reaction was to turn away, but I didn’t. I had to watch this play out. Bill began texting again, and there was no mistake he was sending the pictures to someone, but it wasn’t me.  My phone remained silent. The kitchen door was slightly ajar, and I leaned in to hear the telltale dings of text messages coming and going.

I continued to watch and listen for a solid 10 minutes or more before I burst through the door, demanding to know who he was communicating with and sending pictures of his erect dick. There was no doubt I took him off-guard, but he remained cool, calmly closing the apps on his phone and placing it between his legs as he covered his still erect cock with a towel.

Bill had the audacity to deny he was doing any such thing, which only incensed my anger even more. “How can you deny it?” I yelled.  “I’ve been watching you for over 10 minutes. I stood less than three feet away as you masturbated, took videos, and texted them to someone!” If he had told me it was Steve, I likely would have believed him and the argument would have been over, but stupidly he said it was not Steve.

Bill continued to deny what I saw him doing, and it quickly turned into the first real fight we ever had in the short nine months since we married. It got loud and vulgar before Bill stormed back into the house, accusing me of being irrational. The accusations of me being irrational and crazy just made an already incredible situation that much worse. I began crying and screaming about my greatest fear of engaging another man was that he would never again be satisfied unless he had the “real thing.” Everything I knew to be true or suspected was met with staunch defiance.

After two days of arguing and another few avoiding each other, we were at a stalemate.  I refused to change my mind about what I witnessed, and Bill refused to talk about it. On more than one occasion, Bill had told me that most criminals in his law enforcement experience were really stupid, but a few of them knew how to survive interrogation and often a conviction – by keeping their mouth shut even when the evidence was obvious. And, that is precisely what Bill did – he refused to talk and stood firm that I did not see what I alleged. His ability to duck, dodge, and deny the truth was amazing.

I was beside myself with frustration and anger, and I was determined to find out what he was up to and with whom. What else didn’t I know but could no longer avoid finding out? The premonitions from the voice inside my head that I had silenced all those months since we met were finally front and center saying, “I told you so.”

The seeds of suspicion were sown. Life as I knew it was going to change drastically from an innocent glance out a window – proving once again the course of one’s life can suddenly change over the simplest of things.

[mylifewithacrossdresser]

Chapter 8: Indecent Proposals I Didn’t Resist

Bill and I comfortably and openly discussed our sexual fantasies all of the time. Bill was quite unapologetic to admit he could get a hard-on just thinking about a ‘tranny’ who looks like a beautiful, voluptuous woman from the waist up, but who is stroking a huge, erect cock. These men are referred to as ‘passable’ trannies because they can ‘pass’ as beautiful women.

Transvestite prostitutes have been known to fool unsuspecting men who pick them up thinking they have just scored a stunning woman.  You might recall in 1991, Danny Bonaduce, the red-head, freckled face child star from the Partridge Family, was arrested for beating up a transvestite hooker, Darius Barney, in Phoenix, AZ. after learning his pickup was a man and refused to return Danny’s $40.

Our sexual fantasies only had a few things in common.  We were both interested in a threesome, but while I was interested in another woman, Bill was interested in a threesome with another man as a playmate for himself. Bill did not divulge this preference right away. It would be six months after we were married in 2015 before Bill would suggest it after posting a profile on a few swinger websites for another woman to engage in pegging Bill produced no replies.

Bill made it clear he was not interested in another couple because most of them would want some form of ‘swapping,’ and he was not at all agreeable to see me with another man. Besides profiles on swinger sites, we also visited a local adult club, but Bill walked in with the demeanor of a cop and was so uptight that neither one of us enjoyed ourselves, and we never went back.

At some point, Bill suggested we try poppers. I learned that poppers are a slang term for a class of chemicals called alkyl nitrites that create a ‘high’ or ‘rush’ when inhaled. Poppers not only have a euphoric effect, but they also relax specific involuntary muscles, such as the anus and throat.  They are commonly used in the gay community and can be purchased legally online or in adult sex stores. I was never a heavy drug user and did not like the idea of inhaling anything, much less something that was once sold as ‘video head cleaner.’

As is my nature, I conducted research. I learned that the Merck Manual of Diagnosis and Therapy reported insignificant hazards associated with inhalation of alkyl nitrites, and they are placed among the less harmful of recreational drugs. [1]

Poppers generally make you feel dizzy or woozy and your face becomes flushed. Some people report that poppers don’t necessarily make you horny, but you can experience a strong head rush and a loss of inhibition that makes sex extremely powerful and intense. In a sense, they do make one horny because of the heightened sense of arousal and sexual excitement you feel. (As is the case with most drugs, I found the morning after headache not worth it.)

All the experimentation with poppers, the increasing size of our sex toys, and the frequency of their use made traditional intercourse seem boring for Bill. While I was thoroughly enjoying my newfound sexual freedom, I was beginning to miss the intimacy of making love with a man I cared about and with whom I hoped cared about me beyond my willingness to strap on dildos.

Eventually, Bill got around to asking what I thought of the idea of trying to find a man as a play partner. Knowing Bill was staunchly against me being in a sexual situation with another man, I knew right away the idea was aimed at finding a play partner for him. Bill claimed he had never been with another man, and I naively believed him.

We talked at length about what this scenario would involve. Bill easily expressed the desire to find another crossdresser or at least a guy who would be open to him being dressed and willing to stroking each other, sucking each other off, and perhaps being pegged by me playing the dom.

Being so eager to please Bill, I agreed with only a slight hesitation. I expressed my concerns that going from large, rubber, squirting dildos to the ‘real thing’ may cause Bill to like the ‘real thing’ too much and would anything but a real cock be a disappointment. Bill assured me that could never happen, so we set forth the boundaries and rules of engagement and even came up with a safe word if either one of us got uncomfortable we could signal the other to stop or change directions immediately.

Instead of using the swinger sites we had been on, Bill suggested we use Craigslist Personals[2], which I had no idea existed. (Oh, how naïve I had been all those years!) I thought Craigslist was where people went to sell used cars and furniture – not to find sex partners.

Bill pulled up the Personals section, and I was shocked at the nature of the propositions, the ads’ graphic descriptions, and the sexually explicit photos that Craigslist allowed to be posted. When I asked Bill how he knew about these swinger sites, adult clubs, and Craigslist, he always associated it with his police work and undercover missions. However, when he wrote the ad, he seemed to know exactly how to use the filters and craft it in the familiar language of this unique community.

Within 24 hours we had multiple replies. One response seemed to be exactly what Bill was looking for.

[1] O’Malley, Gerald F.; O’Malley, Rika (January 2016). “Volatile Nitrites”. In Porter, Robert S.; et al. The Merck Manual Online. Merck & Co. Retrieved 2017-09-16.

Nutt, D.; King, LA.; Saulsbury, W.; Blakemore, C. (March 2007). “Development of a rational scale to assess the harm of drugs of potential misuse”. Lancet. 369 (9566):

[2] In March 2018, Craigslist shut down its “personals” section to avoid potential criminal and civil liability after Congress passed the Fight Online Sex Trafficking Act. Plenty of alternative sites filled the void.

[mylifewithacrossdresser]

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 unorthodox and erotic 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. Bill said he 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 appears to be 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. Bill alleges it was 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’s tolerance and willingness to engage in the type of sexual activities Bill was interested in, he 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 – gay porn that is. 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 with women from the PD, 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 and conflicting explanations, 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.

[mylifewithacrossdresser]

Chapter 6: If It’s Ugly, Don’t Look

My relationship with Bill involved much more than just the sex and his crossdressing. We enjoyed many of the same things, such as travel, sports, and physical fitness. We shared the same goals and priorities, positions on finances, career aspirations, and religion.  We both preferred a 5-star resort over a tent but relished the unique beauty of our desert terrain and the outdoors. Neither of us had been looking for love, but it seemed like love had found us.

Bill was not put off by me having such a young son even though his full-time parenting days were essentially over with his youngest daughter attending college in the fall. Casting caution to the wind, I was all in when Bill suggested we move in together during a trip we took with Brian to Hawaii only two months into our relationship. Things were moving fast, and like so many of us who think they’re in love, I put blinders on to the signs of potential trouble.

Trust was always a colossal factor in my eagerness to participate in the sexual games we played, and Bill never proposed anything I wasn’t comfortable doing. Although I supported Bill’s crossdressing as his way of self-expression and played the role of dom during our sexual activities, Bill conducted the direction we took by suggesting the next level of sexual engagement. These suggestions included joining online swinger sites and visiting local adult clubs in search of a playmate to join in our escapades.

All of the bedroom adventures were fun, exciting, and different. It was a special feeling to know Bill trusted me with such personal secrets and fantasies. I wanted to please Bill but it became too obvious to ignore that any time Bill and I engaged in sex, it was always centered around his dressing and role-playing.  He didn’t ignore me completely, but whenever the focus turned toward my arousal or sexual satisfaction, it was always by way of a vibrator or other sex gadget.  Bill avoided penile penetration, and I could tell he struggled on those rare occasions where I maneuvered him into it. Everything mostly worked okay, but the intimacy when it was just him and me with no toy, panties, or shoes was extremely uncomfortable for him.

Attempting to broach the subject on several occasions always resulted in a denial and an excuse. I tried being very direct by explaining that I loved everything we were doing but not every time. Once in a while, it would be nice to wake up on a Sunday morning, roll over, and just make love instead of fuck.  Bill said he agreed and wanted that too, but it rarely happened – not even during eight days in romantic Hawaii where we had no toys for fear of our bags being searched by TSA. Without the pageantry and the props, Bill tried to avoid sexual contact altogether.

My own avoidance tendencies were in firmly place as I plunged further into BDSM in order to please Bill. Putting aside my hurt feelings, my own sexual needs, and my desires for affection, I continued to move forward toward a new life with Bill and all that it entailed. Avoiding the obvious was a short-term solution to a long-term, complex problem. Some things are just too ugly to look at.

[mylifewithacrossdresser]

Chapter 5: Lessons in Erotica

The first time I saw Bill fully “dressed” was two weeks after he revealed he was a crossdresser. It was his turn to stay at my house during Brian’s week with his dad, and Bill brought several bags stuffed with his outfits. No doubt all those size 12 women’s shoes took up a lot of room.

The first evening of his stay, he disappeared into the bedroom for almost an hour. When he emerged, I heard the “click, click, click” of the high heel shoes as he made his way across the stone tile floor toward the kitchen where I was making drinks.

Bill came around the corner dressed in black, platform, high-heel shoes, matching black, thigh-high fishnet stockings, and a tight-fitting, hot pink teddy. I was thankful he wasn’t wearing the wig or makeup.  My initial reaction was mixed. On the one hand, Bill looked absolutely ridiculous, but on the other, he looked rather spicy.  He had long, shapely legs that most women would die for, but the contrast of his masculine shoulders bulging from the teddy was an odd sight.

Bill didn’t look or act womanly at all. There was nothing effeminate about Bill’s mannerisms whatsoever, whether he was dressed or not. He walked a little slower because of the shoes, and he swayed his hips ever so slightly for effect, but he still had that upright, commanding posture of a cop, and his mustache and goatee made him look all the more manly.

Bill was tense and nervously asked if I thought it was too weird. Indeed, it was strange, but I tried to put him at ease by telling him I thought it was sexy. I also looked him straight in the eye and said that he was an adult and had the right to live his life as he chose, and I would not judge him for simply enjoying the feel of feminine clothing. I truly meant those words. It all seemed confined to the privacy of the bedroom and was not something he did in public. And, so long as he didn’t hurt anyone or engage in something illegal, I saw nothing wrong with his fetish. Not yet.

Bill made it easy for me to shed all the inhibitions I had about my body and sex. At 50 years of age, I was in the shape of my life and finally felt free to express myself in intimate situations and not feel self-conscious. I enjoyed the sexual freedom that came from my relationship with Bill even though it involved some unusual elements.

I was so eager to please Bill that I not only indulged his fetish of wearing feminine clothing as part of our sexual activities, but I immersed myself in the role of a dominatrix and the world of BDSM and erotica.  I bought special leather clothing and learned how to talk like a dom giving commands with confidence. I became skilled at giving sexual pleasure to the edge of pain.

Bill not only liked to be dominated in this way, but he also wanted to be humiliated during our role-playing. He had no problem being spanked with a paddle, having a collar and chain around his neck, and loved to have nasty words written on his butt. (By the way, Sharpie pens don’t wash off for days.) Bill loved the terms cock slut, cum dump, and sissy.  It all felt funny at first, but I got used to it with practice.  To me, it was just private fun and games. However, I would soon learn that to Bill, it was serious business and meant far more than having some erotic fun.

[mylifewithacrossdresser]

Chapter 4: The Full Monty

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 pink 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 quickly 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 time 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? What else was he hiding?

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 on crossdresser websites, 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.

(The term “The Full Monty” is an informal British slang term that means it is as complete or extreme as possible.)

[mylifewithacrossdresser]

Chapter 3 - The Badge, Bottles, and a Box

Meeting people through an online dating service is a risky business. Coming off a 15-year marriage, I certainly wasn’t looking to fall in love – I was just trying to have a little fun. I was very careful with whom I communicated and even more cautious about who I was willing to meet in person. More importantly, I had an 8-year-old son to think about and was not about to parade men in and out of Brian’s life. Bill was the only person I met online I ever introduced my son to during the six months I used the service.

Bill gave me no cause for concern about a criminal background or a hidden drug problem when he revealed he spent 25 years in law enforcement, served on the SWAT team for 20, and retired a Commander. He was financially secure, owned his own home that he kept in immaculate condition, was a father of two successful daughters, and was working on a second career with one of the state’s largest employers. His organized and responsible life, only intensified the attraction I was developing for him.

Within a short time after we met, Bill invited me to spend a week at his house while Brian was with his dad. I worked remote so I would spend the day working at Bill’s kitchen table while he commuted downtown. Bill gave me the use of a closet and the extra medicine cabinet in his master bathroom to store some personal items. On the top shelf of the medicine cabinet, there was a collection of nail polish and a tube of lipstick. Naturally, I assumed they were left behind by his previous girlfriend with whom he said he had broken up several months prior. I thought it odd there would be so many bottles of polish as the only effects she would leave behind, but I shrugged it off without comment or question to Bill. It was none of my business.

The second morning of my stay before Bill left for work, he invited me to check out the contents of a box he kept in his top dresser drawer. He didn’t offer any details and I didn’t ask any questions. Even though I was going to spend time at his house alone, the only drawers I felt comfortable opening were in the kitchen. I forgot all about the invitation to look in the box.

During dinner, Bill nervously asked if I had checked out the box, to which I replied no and explained I wasn’t comfortable opening his drawers. For the life of me, I couldn’t figure out what could be in that box that was so important he kept bringing it up.  It made me not want to know what was inside.

Bill led me to the bedroom and placed the plain, cardboard box on the bed and told me to open it as he took a step back to watch from behind. The contents were an assortment of clothing – underwear mostly but not the type Bill had been wearing. This collection was different.  These items were colorful and flamboyant with lace, bows, and red hearts to give them a distinct silky, feminine look and feel. The one item that stuck out from the rest was a flimsy, white kind of thong with silver sequins sewed on the front panel. Another was a short brief style but made out of see-through hot pink mesh material.

I knew Bill had some unusual sexual fetishes and liked being a “sub,” but seeing this feminine underwear was still surprising. Bill was watching me intently, but my back was still toward him so he couldn’t see my furrowed brow as I tried to make sense of what this meant. Bill asked what I thought, and the only safe thing for me to say at that point was why it was hidden in a box, to which he replied it was to keep them from the prying eyes of his youngest daughter or housekeeper. He also volunteered that he liked to wear them because they made him feel sexy.

When I didn’t react with shock or laughter, he asked me if there was anything that I wanted him to try on. I felt awkward, not sure how to respond to the confusion I was feeling. I picked up the white thong with silver sequins, and Bill took that as my selection. Later, when he came out of the bathroom with nothing on but his silver sequined thong, I wasn’t sure what to make of it, but I played along with the show.

This was the first introduction to a much deeper appetite for role play that would become the mainstay of our sexual relationship for the next several years. That night, I noticed something slightly different in Bill during sex that I hadn’t felt or seen before.  He was getting close to being in his true element. But there was more – much more.

[mylifewithacrossdresser]

Chapter 2 - A Glimpse Behind the Pink Curtain

Bill and I met through a popular online dating site. We met at Starbucks, which seems to be a popular first date venue used by the online dating crowd. We started at Starbucks in the early afternoon and ended at my house in bed before 10 p.m.

The sex was fiery hot, physical, and without the slightest inhibition. There was none of the usual awkwardness people often experience the morning after first sex. Bill hung around until Noon the next day, staying for breakfast, a dip in the pool with my dogs, and long conversations about our jobs, our past, our interests, and where things might be headed between us. It was the perfect ending to an incredible first encounter. There was nothing unusual about that first sexual encounter, but I noticed that Bill shaved his legs, chest, armpits, genitals – his entire body was devoid of hair except for his head and a trim goatee. I noticed but didn’t think much of it.

There was instant chemistry between us from the moment we met in person. It was clear to both of us that we were not going to take things slow. Some call it love at first sight or crazy stupid, but whatever you call it, we had it. From that first date, we were inseparable.

Within days of our first date, Bill began testing my acceptance of certain things he was drawn to, including what my appetite was for his particular variety of sexual interests. While Bill wore traditional men’s boxer shorts the first time or two we slept together, he quickly tested my tolerance for his preferred underwear of choice – thongs.

He started by asking subtle questions over text messages such as “Boxers, briefs, or other?”  Confused, I replied, “Other?” and his response was “Thong.”  When I replied, “Sexy!”, I never saw the boxers again unless he went to the doctor or worked out at the gym. At first, he wore a collection of mostly black and blue thongs designed for a man’s anatomy that were not at all feminine. They were much smaller than a speedo bathing suit, but you get the idea.

The testing continued with a question about toe rings.  Mistakenly, I thought the reference was whether I wore them, but he corrected me and asked whether I minded if he wore toe rings. I replied no. The next time I saw Bill, he had one silver toe ring on each of his middle toes. I had never seen a man wear thongs or toe rings before, but I didn’t think it was so unusual that I would never want to see him again. However, these subtle and quirky situations were making me more curious by the day.

The inquiries to test my tolerance started innocently enough with underwear preferences but quickly escalated to sexual desires and fantasies. Within a week of our first date, Bill bravely asked me over a text exchange if I ever tried ‘role-playing’ or ‘pegging[1].’ I played along and it led to a very steamy, blow-by-blow account where I described in detail restraining him to the bed, strapping on a dildo, and slowly pounding his ass until he exploded. He was quite thrilled with my erotic story, which was soon recreated in real life when Bill brought out some of his adult toys, including a strap-on harness and an assortment of dildos, butt plugs, and restraints.

Bill made it very clear that he liked to be dominated by a woman and to be in a subservient role during sex. He had a deep desire to be humiliated, spanked, and called dirty names. While he had not yet revealed his crossdressing, his submissive role during sex quickly became the norm when he described that “man on woman” intercourse “never did anything for him.”  Again, I had knowledge but no understanding of how that declaration would impact and change my life.

Bill had given me just a glimpse of what was behind the curtain, but there was so much more backstage I had yet to see and experience.

[1] Pegging is a sexual practice in which a woman performs anal sex on a man by penetrating the man’s anus with a strap-on dildo.

[mylifewithacrossdresser]

Crossdressing: The Facts and Other Interesting Stuff

What do you know about crossdressing?

The original term for crossdresser is transvestite, from the Latin word trans (meaning ‘across’ or ‘to cross’) and vestire (meaning “to dress” or “to clothe”).

The term transvestite to describe people who habitually wore clothes of the opposite sex was first used in 1910 by Magnus Hirschfeld[1], a German-Jewish physician, and sexologist who was an outspoken activist for sexual minorities. Today, the use of the word transvestite to describe heterosexual males who wear traditionally feminine clothing is generally viewed as an offensive term as it was once used to diagnose medical and mental health disorders, which included a psychiatric diagnosis referred to as “transvestic fetishism.”[2]

A more derogatory term is ‘tranny’ which is a slang word used mostly in the pornographic industry. Other terms include panty boy, sissy, CD, shemale, and fem dom.

The more common and acceptable term of crossdresser first appeared in the 1970’s and was specific to describe people who wear clothing designed for the opposite sex. The term is not intended to suggest a motive or cause for cross-dressing behavior nor is it intended to refer to one’s gender identity, but rather to describe the act of dressing in clothes associated with the opposite sex.

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. Transgenders 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.

[1] The Transvestites: The Erotic Drive to Cross-Dress (1910), Prometheus Books; translated by Michael A. Lombardi-Nash (1991)

[2] The DSM Diagnostic Criteria for Transvestic Fetishism. American Psychiatric Association. 2009. Retrieved February 4, 2013

Men who cross-dress 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, your pastor, your neighbor, your favorite football player, your father, or even your husband, and you may never know it.  They are professional athletes, soldiers, businessmen, construction workers, teachers, politicians, cops, and store clerks.  They are everyone and anyone.

Crossdressers should not be confused with Drag Queens who dress as women (usually celebrities) as part of a paid, theatrical performance. The motivation is different.  One is a profession, the other is an obsession.

A common question is “are crossdressers gay.”  First, not every gay man is a crossdresser and not all crossdressers are gay. However, I believe many of them are gay or are sexually attracted to men, but will never bring themselves to acknowledge or admit it.

Crossdressers generally do not associate themselves with the LGBTQ community because they allege, they are straight heterosexual males who simply like to dress in woman’s clothing. Most crossdressers do not identify themselves as being gay and they are not transsexuals in that they do not see their biological sex as being wrong. Indeed, there are homosexual crossdressers, but they are allegedly the minority. Or so they claim.

While some men have motivations to crossdress other than for sexual arousal there are many who do it for sexual stimulation and it is referred to as ‘transvestic fetishism’[1] However, just like some people watch porn for sexual arousal, crossdressing is not abnormal or illegal, and the medical profession generally does not treat people for it because they typically lead normal lives and are not harming anyone or themselves through the behavior. However, great harm can come if a wife or significant other finds out and feels betrayed.

Not only do crossdressers enjoy dressing in feminine clothing, but many of them adopt a feminine name to go along with their alter ego. Profiles posted by CDs and TVs on the popular website CrossdresserHeaven.com, often use a feminine name to identify the member as do the websites and blogs managed by CDs and TVs. There is no shortage of websites dedicated to this community and it is unusual not to see a profile that is not reflective of the CD’s feminine personality.

[1] BLANCHARD RAY. The DSM Diagnostic Criteria for Transvestic Fetishism. Arch Sex Behav [online]   December, 39(2):363-372 [viewed 22 July 2014] Available from: doi:10.1007/s10508-009-9541-3

The reasons why men engage in crossdressing are as varied as the men who do it. Everything from sexual gratification, relief from stress or PTSD, 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 – they just like doing it.

A 2008 posting on Crossdressers.com displayed the results of an unscientific, online survey of crossdressers conducted in 2001[1]. While not scientific, the results of more than 500 responses were fascinating.  For example, the survey concluded that the average age of these men’s first experience with cross-dressing was age 11.

Their familial status was also interesting with 54% of them being married and 73% of the married men reported their wife knew of their crossdressing. I was not surprised at the 42% who responded the reason why they continue to crossdress is for sexual excitement and that another 42% do it daily with panties, bras, and pantyhose being the clothing of choice.

[1] https://www.crossdressers.com/forums/showthread.php?81693-Crossdressing-Survey-from-2001

My experiences and the unexpected impacts of being married to a crossdresser are detailed in the series of Chapters. The story makes more sense if you read the Chapters in sequential order.