Cruising for a Bruisin' Ch. 01

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Living en femme full time isn't for me.
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komrad1156
komrad1156
3,765 Followers

*Note to readers: After writing The Agreement, I had several people email me and ask why I don't go full time. The answer is very simple: I like being a guy. I only want to be a girl part-time. I've never had any interest in being a woman, and any thoughts along that line were completely dispelled after going on a cruise with a former boyfriend.

Whenever I write in the first person, the story is based on personal experience. Most of those experiences with regard to crossdressing have been positive. But it's not always sunshine and lollipops in drag. I'm an optimistic person, but there's a downside to everything, and I try my level best to write honestly about the good, the bad, and the ugly. It would be both easier and more interesting for the reader if I made everything sound all hunky dory. But not everything goes according to plan, right? In my male life, my dream marriage ended in divorce, my best friend was killed in Afghanistan in 2008, and my mother died from pancreatic cancer at an age that was much too young. Bad things happen to good people and then there's my favorite: shit happens. It's a kind of corollary to Murphy's Law. So while this story isn't macabre or even a "Debbie Downer", it's an accurate recounting of what happened and not all of it was fun and exciting.

As to the trip overall, the first day was exhilarating! I loved flying back home to Seattle as a pretty girl with my then-boyfriend, Tim. Initially, everything was an interesting, new adventure from the boarding process at the Dulles airport to checking in to our cabin onboard the cruise ship. It was exciting to dress for the flight, then for dinner, and it was wonderful making love late into the night. The next day was also fun. Getting made up—again, dressing up—again, having breakfast and lunch in public, spending the day looking around the various shops on the ship, and again wearing semi-formal attire for dinner. But by the third day, I was getting tired of sitting up straight, smiling all the time, crossing my legs, watching myself constantly with regard to gestures, the way I walk and talk, and being pleasant all the time. I'm not an unpleasant person, but pleasant is different for men and women. There are exceptions, but generally speaking, women smile MUCH more than men. They laugh more, too. Keeping that up when it doesn't come naturally is a...bear.

By the fourth day, I was sick and tired of being a girl. By the time I got home, I couldn't wait to get out of my female clothes, get the makeup off my face, put on a pair of shorts and a tee-shirt, drink a beer, belch, and scratch my balls and ass whenever I felt like it! Okay, I don't normally scratch either of those places, but I wanted to just because I COULD! What I wanted the most was to completely slouch in a big, comfortable chair with my legs spread wide apart and be a man again.

So with that caveat, I decided to share my experiences—all of them.

*****

Chapter 1

"Dude, why do you have two cells phones with you? You're not married, so what the fuck?"

I quickly went back to the home screen after reading a text from Tim. There was no way I was going to tell the guys at work I'm a crossdresser and date men on the weekends. I and most of my co-workers are civilian contractors on a Navy base in Virginia. We're not active duty types so it doesn't matter who we date and besides, "don't ask, don't tell" had been repealed so dating men wasn't an issue regardless. But let's be honest. Crossdressing is one of the most misunderstood and maligned behaviors in America (or anywhere else it's practiced.) People are now mostly accepting or at least quietly tolerant of homosexuality and thanks to Bruce-turned-Caitlyn Jenner, transsexualism is getting a fair amount of exposure. But crossdressing and crossdressers aren't familiar to most people which makes for a lot of jokes and misunderstanding. So I choose to keep my private life private.

"Keep this between you and me, but I'm working undercover for the CIA," I replied.

"Yeah, right. And I'm James Bond," Kyle Greer quipped. "It's no big deal to me. It's just kinda odd to have two personal cell phones, but whatever."

It really was weird in at least one sense. I buy a new burner phone whenever I have a new boyfriend and he's the only one who has that number. When we break up, I toss the phone. What's "weird" about it is that when dressed as a man, I have zero interest in men. I am totally straight, only into women, and never even think about any guy 'that way.' But once I'm in drag, I am (almost) only interested in men, and am 'totally straight' in that regard. No, I'm not delusional. I'm fully aware I'm a bi-sexual male playing girl a few hours at a time once or twice a week or occasionally for a weekend. Call it whatever you like, but that's the way it is where my interests in men and women are concerned.

Before I started crossdressing (again) I was an avid weightlifter. I was in the gym nearly every day for years starting in my junior year of high school. I'd been overweight and had horribly misaligned teeth growing up and never been on a date until my senior year. In fact, the change was so dramatic I went from being ignored on my best days to humiliated by the popular kids on my worst to being hit on non-stop by nearly every girl who didn't know I was alive since the time I became invisible in the 3rd or 4th grade. I had an affair with my English/creative writing/mythology teacher which I wrote about in a story I call Creative Writing as well as with a lonely Mormon woman I shared in Bagging Lauren.

After my interest in crossdressing came back with a vengeance, I stopped lifting literally overnight and started running seven days a week. It took me nearly six months to lose enough muscle mass to get to where I could fit into a size 12. It took almost six more months of running and extreme dieting to be able to fit into a size 8 or 10 depending on who the designer is. Now I can wear an 8 in pretty much everything but it takes a lot of work to stay that thin. For people who gain weight easily, I don't expect any sympathy because yes, I can stay thin. But it takes constant attention and very little cheating.

My ex-wife was a wonderful girl who was several years older than me. I "rescued" her (and myself) from Mormonism and helped her become the bad girl she'd always wanted to be. She learned she had a real passion for B&D which I didn't share, but because she did everything else I'd ever dreamed of for me, I played along until I couldn't take it any more. We had several threesomes, tried couple swapping, and I even had her cuckold me a few times only without the humiliation that seems ever-present in stories on that topic. I'd find an attractive, younger guy and bring him to a motel where I'd watch him fuck my wife. I wrote about those experiences in Making Changes and Giving Me Claire. As exciting as that all was, it just got old, tired, and boring. I desperately wanted something new and fresh, but I was well, fresh out of ideas until...

Once my deeply-buried urge to crossdress came back, it was pretty much all I thought about as I quit lifting and starting getting thin. My ex-wife came home unexpectedly once and found some of my things left out. That led to her seeing me dressed up and being genuinely shocked at how I looked. When she found out I was interested in dating men, she used that as an excuse for her to date other men without me being with her. We even double-dated once (and only once and at her suggestion) when I was in drag and that was the beginning of the end of our marriage. That's the gist of the story I referenced called The Agreement. I dated that guy for several months, then met someone else, and finally I found Tim. Or rather, he found me. I shared some of our experiences in Tim and Callie and Dave and Beth. The cruise happened about a month after the foursome we had with his best friend Dave, and his beautiful wife, Beth, who looks to me like a twin of the actress Leslie Bibb in her younger days.

I pulled my burner phone out and reread the text. "Hi, honey! I want to take you on a five-day cruise. Will you go with me?" I know I said I'm not into guys when I'm dressed in drab, but if my mind 'goes there', then I can quickly find myself (herself?) fantasizing about being Callie and being with the guy I'm dating. I'd been staring at the text when Greer asked me why I had two cell phones. I was imagining going shopping for a bunch of pretty new things and spending an entire five days as Callie! I was sporting a partial woody under my Levis when Greer broke me out my trance. Later on, I texted Tim back that it sounded very exciting, but I told him it couldn't be anywhere that's hot and humid. Tim immediately understood why.

First of all, I have a sweater fetish that won't quit. I love pretty dresses and other frilly stuff, but growing up near Seattle and seeing girls wear them nine months out the year, I am a sweater girl through and through. If it's form-fitting, preferably (but not necessarily) rib-knitted, and sexy looking, I'm buying it. I won't wear some baggy, clunky, multi-colored, hideous-looking thing, but if it looks like my kind of top, it's mine. Sleeve length doesn't matter. I like sleeveless, cap sleeves, short sleeves, 3/4-length, and long sleeves. As long as it's in my clothing wheelhouse, it's coming home with me. Yummy, yummy, yummy!

Secondly, I am, after all, a man. Men sweat more than women—a lot more. There's simply no way I could even sit, let alone walk around, in heat and humidity in drag for more than a few minutes at a time. I'd be a sweaty mess in short order and it would draw attention like nothing else.

You can see my 2010 blonde wig pics and compare them to my 2015 brunette pics with my own hair (plus nose job and some other cosmetic changes) and decide how passable I am. Considering I've never once been "clocked" in public, my sense is I do pretty well. But women don't drip sweat the way men do, so most of my summertime forays into the world as Callie are done in the evening or where there's air conditioning at all times.

"How about Alaska?" he texted me back. He was suggesting a cruise in September so it would be getting cold but wouldn't be freezing cold yet. I went on line and checked out the average temps and started getting excited!

"Sounds perfect!" I wrote back. "Need to discuss details, okay? Love you, Callie."

It was Wednesday afternoon and we had a date for Friday evening. Tim was taking me out to dinner and then dancing at our favorite local spot called The Blue Parrot at the Hilton Hotel in Springfield, Virginia.

I don't have any friends who are crossdressers, but from what I understand, most enjoy getting ready as much as I do. It's just SO exciting to get a total body wax, come home and lay out what you're going to wear, then shower, and do your makeup. It's almost like being in a trance. Many years ago, I read a book called Flow by author Mihaly Csikszentmihalyi. Flow is the author's term for the state we get in when we're so into something, we're unaware time is passing. We become so absorbed in what we're doing, time begins to just...flow. That's exactly how it feels every time I sit down and start doing my makeup.

I love the simple yet complex challenge of blending everything together to make my face and skin tone look perfect. Liquid foundation, concealer, highlighter, getting the eyebrows perfect, blending eye shadows, applying false eyelashes, mascara, blush, and a finishing powder. I get so excited just thinking about it. Doing it sends me into another world. You girls know exactly what I'm talking about, right?

Before I grew my own hair out, the finishing touch was putting on a wig I'd carefully combed and styled. The moment it went on my head, I felt myself turn into Callie. For the next few hours, I was a woman or at least felt like one. The icing on the cake was dressing in the pretty clothes I'd laid out, putting earrings into my pierced ears, and finally stepping into a pair of 3-4" heels. O...M...G! What a thrill!

And for those of us lucky enough to be able to go out in public, we have the joy of going somewhere and showing off our best self. Most women don't dress to the nines so there are only certain places you can away with it without drawing unwanted stares. Dinner and dancing on the weekend is a perfect opportunity to do just that.

It was still summer, but the evenings were beginning to cool off a bit and any relief from the hot, humid days in Virginia was most welcome. For our night out, I choose a white, sleeveless, rib-knit top by Calvin Klein and a short, suede A-line skirt from Belk. I paired a pair of cute taupe-colored shoes with 3" heels with a matching purse and finished the look with a gorgeous gold and onyx necklace/bracelet/earring set that I loved and which looked fantastic with the outfit. Lastly, I carried a pretty white cardigan on my arm as it often got chilly inside.

Tim arrived at 7:30 as he'd promised. "Hi!" I said as I let him in.

"Jesus, you look so amazing, Callie!" he said as he kissed me hello.

"Thank you!" I told him sincerely. I loved being pretty for him and I knew he appreciated it, but it was still nice to hear him tell me so. Tim had never dated a crossdresser (or any man) before me and I was so smitten with him I felt like I'd won the lottery when he noticed me at Screaming Queens. A very non-passable girl sitting next to me told me some handsome guy was staring at me but when I saw him, my knees went weak! He looked like Matt Bomer from he TV show White Collar. He was still legally married but had plans to file for divorce which he did shortly after our first date. Oh, and he's a very successful attorney. Did I mention he's handsome as hell? :-)

"So where are you taking me tonight, sweetheart?" I asked him while my arms were still around his neck.

"I hope you like Mexican because I have reservations at Oyamel," he said as he flashed his dazzling smile at me.

"Oh, my goodness!" I said. "I've wanted to go there for the longest time! It's on the top 5 list every year."

"I know. It's tough to get a table but I know someone who knows someone so..."

I kissed him again and said, "Someone is definitely getting lucky tonight."

We headed downtown and eventually for 7th Street in Northwest. It was such a beautiful place that was both luxurious and inviting. As we stepped inside, we were greeted by a very nice-looking young man who said, "Buenas noches, señor y señora! Bienvenido's a Oyamel." I wear a large, cubic zirconia ring on my left hand when I'm dating a guy I really like and I'm hoping that's why I was called señora rather than señorita. I hope it wasn't due to my advancing age. Ugh!

I always let Tim order everything for me so he started us off with margaritas and tortilla chips with guacamole which was superb! For dinner, he ordered Postaza con Mestaza and for me, Cayo con Salsa Negra which is a dish of seared scallops with wild mushrooms, cauliflower, and a black bean chipotle chile. Everything was absolutely delicious!

As we ate, Tim pulled out his iPhone and scrolled through some photos from the Princess cruise line. "These are amazing!" I told him. There was only one five-day cruise. All of the others were 10 or more days and I had no interest in being a girl that long! Little did I know that just five days would push me to my limits, but it seemed very reasonable at the time. Oh, we had to fly to Seattle first so that meant one extra day on both ends in drag along with all the potential hassle from TSA even though I was very careful to tell everyone with whom I spoke I was a male traveling in female attire. Government efficiency—an oxymoron if there ever was one!

"So can I book us?" he asked with some impatience.

"Well, I think I could manage to break away from work for a week so...yes. Go ahead!" I said excitedly. That was near the end of the fiscal year and things tended to get a bit slower and besides, no one else had put in for vacation so I had no trouble getting a full week off.

Tim knew I made good money as an engineer, but he understood that being treated like a real woman was part and parcel of dating me. He was always happy to pay for everything and I have to admit I enjoyed letting him. It was no different than waiting for him to open my car door and help me out or to open a door to wherever we were going. That's just what any gentleman does for any lady he's with.

Even so, when I caught a glimpse of the total price, I gasped. "Okay, I'm paying for the air fare, honey. No arguing." Tim tried saying he had that covered, but I wouldn't hear of it. I pulled out my phone and bought us two round-trip, business-class tickets to Seattle for the 17th of September and returning on the 23rd. "Done!" I announced proudly.

Tim leaned over and kissed me. "Thank you, sweetheart. Did you know I love you?" he said as we ended our kiss.

"I do," I said sweetly. "And I love you, too."

Just then, we noticed our server standing there with the check. "Sorry to interrupt," he said. "Are you two newlyweds by any chance?" he asked.

Tim smiled and looked at me. I winked letting him know it was okay. "This is my beautiful new wife, Callie." I held out my left hand and showed off my (faux) diamond ring with some modest amount of flair.

"A beautiful ring for a very beautiful young woman," he said gallantly. "Can I get you two anything else tonight?" Tim ordered an after-dinner drink and we sat and made small talk while we sipped it.

At around 9pm, Tim said, "The band ought to be into its first set by now. You ready?"

"Definitely. And thank you dinner, honey. It was wonderful."

Tim came around and helped me out of his Lexus as we pulled up in front of the Hilton. "Be right back, okay?" he said as he kissed me on the cheek. He saw me shiver slightly and helped me pull my sweater on before suggesting I wait inside while he parked the car.

"No, thanks. I'll be okay out here," I assured him.

Tim paid the $15 cover charge for each of us and led me into the lounge area. There was a very good local band playing a series of golden oldies which meant music from the '70-'90s. They played one great song after the other and the lead singer had an incredible voice. She was talented and very attractive.

We danced a half dozen times. Some fast, some slow. While we were sitting at our table and sipping a glass of wine, I noticed two good-looking guys staring at me and talking to one another. One of them turned to the other and said something which made him raise his eyebrows. He then high-fived his buddy who walked over to our table. Without looking at Tim he said, "Hi. I'm Eric. I was wondering if you'd like to dance."

I looked at him then over at Tim who looked back at me before addressing Eric. "My wife's a big girl. She can dance with whomever she wants."

Eric was a pretty big guy and Tim is as cute as Matt Bomer but built like him, too. In other words, he's not the kind of guy who's going to fight for the honor of his woman because he would almost certainly get his ass kicked! I smiled at Eric and said, "No thank, you. I'm very much in love with my husband." Without flashing it as I'd done at the restaurant, I let Eric see it.

He glanced down at it and said, "That's okay, I'm not gonna propose to you. I just wanted to dance."

I put my hand over my mouth as I laughed. I looked over at Tim and said, "Do you mind?" I could tell he didn't and after having let his best friend fuck me a month ago, I knew it would be okay. Besides, I'd been to the Blue Parrot several times by myself when I was still wearing my blonde wig. I'd been asked to dance dozens of times and not once did any guy ever so much as hint he might know my secret so I felt very safe dancing with this very tall, very muscular, very cute guy who believed I was a married woman.

komrad1156
komrad1156
3,765 Followers