By the Grace of Guile


*Author’s note: Several years ago, I read an interesting book by author Loyal Rue, a professor of Religion and Philosophy at Luther College, called By the Grace of Guile. An excerpt from one review says this: “For people who are troubled by a world increasingly filled with the sweet-talking duplicity of politicians, preachers, advertisers, and sundry hucksters, Loyal Rue has a cheering message: don’t worry, deception is simply a part of the natural order of things. In fact, deception can actually be good for us. By the Grace of Guile offers a detailed and very learned study of deception, which Rue defines as “the problematic distinction between appearance and reality.”

His book is devoted to examining deception and our efforts to avoid being duped. Deception can be either intentional or unintentional and it is everywhere. The bottom line is everyone uses deception to some degree and everyone hates being duped. Therefore, we expend enormous efforts to keep that from happening whether it’s at the level of one country spying on another to making sure the person we love is being faithful. It takes a very skilled person to dupe most people and avoiding deception requires being very alert and aware at all times. Even then, most people can be fooled some of the time.

As they say, buyer beware.


I’ve written about my crossdressing exploits numerous times and I’ve alluded to some things I did just before and after my first and only double date with my now ex-wife. (That story is detailed in The Agreement.)

I chose not to share them until now because frankly, doing so exposes me as a hypocrite. That said, I don’t know of anyone who isn’t a hypocrite in some way at some degree. Most people just refuse to admit the truth. They’re quick to point out hypocrisy in others but minimize or outright dismiss it in their own lives.

My creed is simple: don’t lie, cheat, or steal. Being misled and acting on bad information isn’t lying but deceit is a form of lying because it has the same necessary element which is intent.

A perfect example is whether or not former US president George W. Bush knew there were no weapons of mass destruction in Iraq and lied to take his country to war or whether he genuinely believed the assessments of the CIA and MI5-6 and acted on them in good faith with tragic consequences. Partisans on both sides of the issue, with access to the same information, still passionately cling to one view or the other allowing no possibility for their conclusions to be wrong.

My earliest attempts at crossdressing in public were most definitely deceitful as I intentionally passed myself off as a genetic female with the intent of getting men to dance with me and, well, as you’ll read, do a lot more than just dance. All of them willingly ignored any clues which might have tipped them off and I have to admit any one of these adventures could have ended with me in the ER or the morgue.

Whether I was a lying, deceitful bastard or a very successful duper is for you to decide. Regardless of how you may feel about what I did, I hope you enjoy reading about what happened back when I was wearing the blonde wig in my 2010 pics on my home page and trying to figure out who I was and what I wanted just before and during my divorce proceedings.

For the record, I am now always completely open and honest about who I am when dressed as Callie. However, it’s a moot point for now as I’m living with a genetic female who is admittedly gay with bi-sexual interests. She loves me for who I am, and I love her just as she is. Our story is told in Serendipity.

I have no idea what’s behind the psychology of crossdressing. For the longest time, I really wanted to know why I was this way. What caused this? What made me this way? At some point, I quit caring because it doesn’t matter. This is how I am and I’m finally completely comfortable with that. For the record, the so-called experts don’t know, either. They have ideas and theories but no one really knows. And I no longer care.


Not long after my ex-wife and I double dated, we separated and divorced soon after. It was all very amicable, and I wish her nothing but the best. We don’t stay in contact, but I’m sure she’s found a very dominate and dominating male to serve as her new ‘top.’

I chose another path after my interest in crossdressing came back with a vengeance about a year before the divorce. I quit lifting weights and started running and dieting seven days a week. It took me about six months to get to where I was in the 2010 pics on my home page and another year to get where I was and still am in the brunette pics. I also had a nose job and some work done on my eyes. At the time these things happened, I looked like the ‘before’ pics from about six years ago.

Once my ex-wife moved out, I devoted all of my free time, efforts, and money into becoming Callie Petersen. I spent hours suadiye escort watching videos on makeup application for both women and crossdressing males. I even took a class in cosmetology to help me learn how to shade and blend. I bought undergarments that were CAD designed to give my flat butt the shape it needed. I found a place where I could go and get a full-body wax and have my eyebrows sculpted. I developed a template for my eyebrows which allowed me to very precisely fill them in with perfect symmetry. False eyelash application had to be mastered, as well. I practiced with every possible shade of foundation and beard cover as well as highlighters and concealers. I got my ears pierced and wore nearly invisible, large-gauge pieces of fishing line at work to keep them expanded as I was still too afraid to wear earrings to work at that time. I experimented with every kind and color of lipstick and eye shadows made by every makeup company until I found exactly what worked best for me.

I also spent a LOT of time learning to style my wig so that the hairline in front didn’t give me away. Even an inexpensive wig can look good IF you know exactly how to prepare it. However, if it’s not done correctly, even a very expensive human-hair wig is a dead giveaway and no matter how good everything else may be, you will be read. And it’s women, not men, who will read you first. Women see everything. From your hairline to your Adam’s apple to your hands, women see it all. Men will spot the obvious mistakes but if you look very good, they want you to be a woman so badly they’ll ignore the tiny little things that will tip a woman off immediately. To fool them, you have to be almost perfect.

I’d already built up a decent-size wardrobe of women’s clothing, shoes, handbags, coats, and jewelry and just kept adding to it. I’ve shared my absolute fetish for rib-knit tops and cashmere sweaters many times and the majority of what I bought fit that description. I had more skirts than I could ever wear, and an endless amount of expensive heels and purses but just kept on buying.

Lastly, I even saw a voice coach to help me with developing a more feminine voice. I’d practiced at home a lot using techniques I’d learned in videos before I went. After just one lesson she told me there was very little else she could do for me and that was that.

After initially venturing out in my car at night and then walking down a public street with a lot of people around after dark, I finally got up the nerve to go to a mall and look around. I spent about three hours getting ready not including the time it took for a full body wax and showering. I knew not to wear anything too sexy or slutty because women just don’t dress that way in public. That said, if you can’t wear what you like, it isn’t a lot of fun.

Therefore, I chose a tan-colored skirt which fell to about three inches above my knees, a very pretty, very dressy long-sleeved black rib-knit sweater with 2 1/2″ black heels, all of which was perfect for the Fall weather. As I pulled up to the mall and parked my car, I was feeling fairly confident, but still had a ton of butterflies swirling around in my stomach.

I swung my legs out the way women do, grabbed my purse, hung it on my lower arm, and shut the door. I took one last look at my reflection in the car window, smiled, and turned around. Just as I’d practiced countless times, I began walking the way girls walk. While they definitely don’t plod along like men, they also don’t strut like runway models. Getting it right is something else that just takes a lot of practice.

As I approached the entrance, a nice older man said, “Let me get that for you, young lady.” I smiled, thanked him and stepped in. He smiled and told me I was very welcome.

Women smile a lot more than men, and I needed to keep that in mind at all times. I was also aware that I had to force myself not keep looking around at people as though something was wrong which would make people think I had something to hide. After all, I was just another girl out shopping. I went around 6pm when women just getting off work and who are dressed professionally are on their way home. Too much makeup in the middle of the day is another dead giveaway, by the way unless one is going to or coming back from a professional type of job. Sure, there are women who wear full makeup in the middle of the day, but there aren’t many of them and does draw a lot of attention so be very careful with that if you want to try it.

I was unable to not look, but the reason turned out to be a positive rather than what I’d feared. Even after all of the time I’d spent preparing, I still had no idea how well I’d pass in public. I just assumed people might be pointing and snickering and that teenage girls would be giggling. What I noticed was that damn near every teenage boy and man I passed did indeed look at me. The pleasant surprise was that most of them smiled at me and many said ‘hi’. I’d had this yakacık escort same experience many times as a man after I got my braces off in high school and had been lifting weights for about a year. Prior to that, I’d been invisible on my best days and the source of many caustic comments on my worst. So I knew the difference between being ‘read’ and being checked out. I wasn’t being read but I was most definitely being checked out and I loved it!

Everywhere I went, the girls in each shop who met me were friendly and helpful. I never saw anyone laugh or point or say a negative word. I bought earrings and several other small items and had a very pleasant first-time experience. That gave me the confidence I needed to try going out to dinner.

The next week, I spent the same amount of time meticulously preparing, then drove to one of the nicer restaurants in the Northern Virginia area. What I didn’t stop to think about was that very few women go out to dinner alone at a nice place like that. Are there exceptions? Of course. But I was the only ‘woman’ there by herself. It didn’t draw any undue attention, but it was something worth keeping in mind for future reference.

That said, the wait staff was very courteous, friendly, and helpful. I even had one waiter write his phone number on the back of the bill in spite of the fact I was wearing a very large Cubic Zirconia wedding ring on my left hand. For whatever reason, it just seemed exciting to pretend I was a married woman along with all the other pretending going on!

After these two very successful outings, I began looking for the ideal place to try and meet men. Yes, I am very bisexual yet until Kay, my current girlfriend, Callie only ever dated men while Cal dates only women. I’m not delusional, I know they are both me. However, in my mind, they are two separate people with very different interests. I’ve never had any interest in men whatsoever as my male self, but from the first time I ever tried wearing women’s clothes, I felt like a girl and was attracted to men. Yes, I know. Most crossdressers are heterosexual. I’ve known that for years but if I don’t mention it, someone will leave a comment ‘informing’ me on the matter so…

Oh, I never write about it in my adventures as Callie, but since I’m coming clean as it were, let me be completely honest and admit this, too. Callie smokes. Cal, on the other hand would never even touch one.

Many crossdressers have a smoking fetish for reasons I don’t understand, but I am definitely one of them. But because smoking has become so taboo making smokers social pariahs just above child molesters, I omit any reference to it from my CD-ing stories. (Kay hates it, by the way, so that’s really cramping my style. Sorry, honey, but you know the deal.) We’re both distance runners so she’s actually been a very good influence on me. Still… 🙂

I did a lot of research and found a place in Springfield, Virginia called The Blue Parrot. It’s lounge in the Hilton Hotel where local bands play nearly every weekend. The music is loud, but it’s more of an oldies vibe with bands playing cover songs. I checked it out as Cal one evening after work then went back to see what kind of clientele showed up for the live performance. As expected, there were a ton of married and dating couples. To my pleasant surprise, there were also a lot of single guys there, many of whom were very good looking. I paid careful attention to what women wore and saw everything from jeans to very expensive dresses and everything in between. I made the decision to go as Callie the following weekend.

I was very nervous and very excited all week. I was consumed with thoughts of what I’d wear, whom I might meet, and what we might do. Sure, I was aware things could go south, but I didn’t care because this was something I felt compelled to do. Compelled is the perfect word because I had some kind of compulsion driving me to do this. I’d been closeted all my life, then married and not dressing up for several years, and now that I’d had a taste of the crossdressing ‘heroin’ of passing in public, I wanted more and more…and more.

It was already not enough to just drive around or even walk around. It wasn’t enough to go to the mall and buy things en femme. I wanted to be with a man. I wanted to feel like a woman in every way and it never crossed my mind that I was doing something wrong. There was a force driving me, and I was happily caught up in letting it do just that.

It was very cold that night but fortunately, there was no wind blowing. Wind does a number on real hair, but it wreaks havoc on a wig.

As before, I got a full body wax and spent hours on my hair, nails, and makeup. Later I would learn to enjoy going out as Callie and having my nails done by someone else. For now, that was still too daunting to even think about.

No surprise, I chose a short skirt and sweater to wear. The sweater was an off-white cashmere blend with a square neck şerifali escort and three-quarter length sleeves. The skirt was black and fell to a little more than four inches above my knees. I wore barely black stockings with a pair of 3″ black heels with ankle straps. I chose gold jewelry which entailed a gold-rope necklace and matching earrings. I wore a very petite-looking gold watch on my left wrist and some gold bangles on the other.

I owned a beautiful winter-white coat which I wore with a pair of matching cashmere gloves. I drove into the parking lot about ten minutes after 10pm knowing the band had already been playing for a short while. The parking lot was nearly filled to capacity, but I did finally find a parking spot that was about 50 yards from the main entrance. I took a final look in the mirror and got out of the car. The air was very cold, but it was preferable to the Virginia summer heat which induces lots of um…glistening…which melts makeup in seconds.

I went inside and immediately heard loud music coming from the lounge. My excitement was building as I went to pay the cover charge and the cute guy at the table said, “Go ahead. No charge for beautiful women.” I smiled and thanked him then went and checked my coat and headed inside.

As I looked around, I could see that almost every seat was filled and I really didn’t want to sit at the bar. I spotted one empty chair and as I took my first step toward it, and older gentleman gently touched my elbow and said, “Hi, there. Care to dance?”

I was so caught off guard I nearly panicked. I just shook my head and mouthed the words ‘no thank you’ and headed toward the empty seat. I sat my purse on the table, smoothed my skirt and sat down. Within seconds, a pretty young girl approached me and asked me what I’d like to drink. “Smile,” I reminded myself. “And use your feminine voice.”

“Vodka and tonic, please,” I said with a bright smile. I preferred red wine, but one drop on my pretty new sweater and it was game over.

When it arrived she refused my money. She pointed to a very nice-looking guy and said, “That gentleman over there paid for your drink. He asked me to tell you his name is Josh.” I thanked her then looked over and him. He was smiling as he raised his glass and nodded at me. I raised mine demurely and took a sip.

As I sat it down, sure enough, there came Josh. He looked to be about 30-35 with dark brown hair and a very handsome face with maybe a couple of days worth of stubble on it. He was probably about 6′ even because in heels, he was still a bit taller than me and I’m 5’8″.

“Hi. I’m Josh,” he said.

“I know,” I said with a smile. “Thank you for the drink.”

“You shouldn’t drink alone,” he said. My first pick line used by a guy to pick me up! I was absolutely thrilled.

“Would you like to dance?” he asked me.

“Sure!” I told him. I’d reminded myself many times that women don’t leave their purses unguarded at a table but sure as $#%^, I left mine just sitting there because I was so caught up in being asked to dance by this very handsome guy that it slipped my mind. Another thing I thought of and managed to remember was this. “What if you get asked to dance early on and that guy wants to monopolize your time?” I was determined to give my first blow job that night, but I didn’t want to leave this early. I told myself I’d dance a few times with him then look for someone else.

The first song was a fast one and fortunately I had practiced dance moves in front of a mirror many times. As the song ended he reached out for my hand and said, “One more?” I knew the song coming up and it was a slow one. My heart was pounding as I smiled and told him, “Okay.”

I put my right hand in his left as most people do to start a slow song but just seconds later he moved our hands down to his chest. He gently pulled me closer to him and I was thrilled beyond words to have such a cute guy hold me like that. Again, I’m not delusional. I know I’m a guy in women’s clothes, but I felt like a pretty girl who was wanted and desired by a handsome boy. I was suddenly in junior high being asked to dance for the first time by the boy I’d had a crush on all year and it absolutely thrilling.

Thanks to the padded undergarment and some tucking, there was no chance my growing erection could possibly be felt should we press against each other. But I was dying to know whether or not I might be able to feel his so I moved my hand from his and put it around his neck. As I did, his hands went down my back and settled just above my waist. As I hoped, he pulled me closer and I responded. Once I was as tight as I could get to his hard body, I gently pushed with hips hoping to find what I was looking for. Sure enough, I struck pay dirt!

As I gently pushed against him, he pulled back slightly and said quietly (at least as quiet as possible with that much noise), “Sorry.”

I said in his ear, “Don’t be. That felt nice.” As soon as I did, he moved his cock back to where I could feel it again. Once I felt it again, I murmured, “Mmmm. I like that.”

By the end of the song, he was pushing against me pretty hard and I was definitely pushing back. My resolution to wait longer was fading fast.